feat(M41): Envoy target connector with SDS support

File-based deployment for Envoy service mesh — writes cert/key/chain
to watched directory with optional SDS JSON config for xDS bootstrap.
Path traversal prevention, configurable filenames, 15 tests passing.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

.gitignore

@@ -62,6 +62,7 @@ certctl-agent
 certctl-cli
 /server
 /agent
+/cli
 
 # Private strategy docs
 roadmap.md

README.md

@@ -14,66 +14,63 @@
 
 TLS certificate lifespans are shrinking fast. The CA/Browser Forum passed [Ballot SC-081v3](https://cabforum.org/2025/04/11/ballot-sc081v3-introduce-schedule-of-reducing-validity-and-data-reuse-periods/) unanimously in April 2025, setting a phased reduction: **200 days** by March 2026, **100 days** by March 2027, and **47 days** by March 2029. Organizations managing dozens or hundreds of certificates can no longer rely on spreadsheets, calendar reminders, or manual renewal workflows. The math doesn't work — at 47-day lifespans, a team managing 100 certificates is processing 7+ renewals per week, every week, forever.
 
-certctl is a self-hosted platform that automates the entire certificate lifecycle — from issuance through renewal to deployment — with zero human intervention. It works with any certificate authority, deploys to any server, and keeps private keys on your infrastructure where they belong.
+certctl is a self-hosted platform that automates the entire certificate lifecycle — from issuance through renewal to deployment — with zero human intervention. It works with any certificate authority, deploys to any server, and keeps private keys on your infrastructure where they belong. It's free, self-hosted, and covers the same lifecycle that enterprise platforms charge $100K+/year for.
 
 ```mermaid
-timeline
-    title TLS Certificate Maximum Lifespan (CA/Browser Forum Ballot SC-081v3)
-    2015 : 5 years
-    2018 : 825 days
-    2020 : 398 days
-    March 2026 : 200 days
-    March 2027 : 100 days
-    March 2029 : 47 days
+gantt
+    title TLS Certificate Maximum Lifespan — CA/Browser Forum Ballot SC-081v3
+    dateFormat YYYY-MM-DD
+    axisFormat
+    todayMarker off
+    section 2015
+        5 years (1825 days)    :done, 2020-01-01, 1825d
+    section 2018
+        825 days               :done, 2020-01-01, 825d
+    section 2020
+        398 days               :active, 2020-01-01, 398d
+    section 2026
+        200 days               :crit, 2020-01-01, 200d
+    section 2027
+        100 days               :crit, 2020-01-01, 100d
+    section 2029
+        47 days                :crit, 2020-01-01, 47d
 ```
 
-## Documentation
-
-| Guide | Description |
-|-------|-------------|
-| [Why certctl?](docs/why-certctl.md) | Competitive positioning — how certctl compares to open-source and enterprise certificate management platforms |
-| [Concepts](docs/concepts.md) | TLS certificates explained from scratch — for beginners who know nothing about certs |
-| [Quick Start](docs/quickstart.md) | Get running in 5 minutes — dashboard, API, CLI, discovery, stakeholder demo flow |
-| [Advanced Demo](docs/demo-advanced.md) | Issue a certificate end-to-end with technical deep-dives |
-| [Architecture](docs/architecture.md) | System design, data flow diagrams, security model |
-| [Feature Inventory](docs/features.md) | Complete reference of all V2 capabilities, API endpoints, and configuration |
-| [Connectors](docs/connectors.md) | Build custom issuer, target, and notifier connectors |
-| [Compliance Mapping](docs/compliance.md) | SOC 2 Type II, PCI-DSS 4.0, NIST SP 800-57 alignment guides |
-| [Migrate from Certbot](docs/migrate-from-certbot.md) | Step-by-step migration from Certbot/Let's Encrypt cron jobs |
-| [Migrate from acme.sh](docs/migrate-from-acmesh.md) | Migration guide for acme.sh users with DNS-01 scripts |
-| [certctl for cert-manager Users](docs/certctl-for-cert-manager-users.md) | Using certctl alongside cert-manager for non-Kubernetes infrastructure |
-
-> **Next release:** v2.1.0 will be tagged after the full V2 feature suite passes manual QA across all 34 sections of the [testing guide](docs/testing-guide.md). Automated CI (1,471 Go tests + 193 frontend tests) gates every commit; the manual playbook covers integration, deployment, and UX verification that unit tests can't reach.
+> **Actively maintained — shipping weekly.** Found something? [Open a GitHub issue](https://github.com/shankar0123/certctl/issues) — issues get triaged same-day. CI runs 1,536+ tests with race detection, static analysis, and vulnerability scanning on every commit.
 
 ## Why certctl Exists
 
-Certificate lifecycle tooling today falls into two camps: expensive enterprise platforms (Venafi, Keyfactor, Sectigo) that cost six figures and take months to deploy, or single-purpose tools (cert-manager, certbot) that handle one slice of the problem. If you run a mixed infrastructure — some NGINX, some Apache, a few HAProxy nodes, maybe an F5 — and you need to manage certificates from multiple CAs, there's nothing self-hosted that covers the full lifecycle without vendor lock-in.
+Certificate lifecycle tooling today falls into two camps: expensive enterprise platforms (Venafi, Keyfactor, Sectigo) that cost six figures and take months to deploy, or single-purpose tools (cert-manager, certbot) that handle one slice of the problem. If you run a mixed infrastructure — some NGINX, some Apache, a few HAProxy nodes, IIS on Windows, maybe an F5 — and you need to manage certificates from multiple CAs, there's nothing self-hosted that covers the full lifecycle without vendor lock-in.
 
-certctl fills that gap. It's **CA-agnostic** — the issuer connector interface means you can plug in any certificate authority: a self-signed local CA for dev, Let's Encrypt via ACME for public certs, Smallstep step-ca for your private PKI, your enterprise ADCS via sub-CA mode, or any custom CA through a shell script adapter. You're never locked to a single CA vendor, and you can run multiple issuers simultaneously for different certificate types.
+certctl fills that gap. It's **CA-agnostic** — plug in any certificate authority: Let's Encrypt via ACME, Smallstep step-ca, HashiCorp Vault PKI, DigiCert CertCentral, your enterprise ADCS via sub-CA mode, or any custom CA through a shell script adapter. Run multiple issuers simultaneously for different certificate types.
 
-It's also **target-agnostic**. Agents deploy certificates to NGINX, Apache, HAProxy, Traefik, and Caddy — all using the same pluggable connector model for any server that accepts cert files. The control plane never initiates outbound connections — agents poll for work, which means certctl works behind firewalls, across network zones, and in air-gapped environments.
+It's **target-agnostic**. Agents deploy certificates to NGINX, Apache, HAProxy, Traefik, Caddy, Envoy, and IIS (local PowerShell or remote WinRM) — all using the same pluggable connector model. The control plane never initiates outbound connections — agents poll for work, which means certctl works behind firewalls, across network zones, and in air-gapped environments.
 
-For a detailed comparison with CertKit, KeyTalk, and enterprise platforms (Venafi, Keyfactor), see [Why certctl?](docs/why-certctl.md)
+For a detailed comparison with CertKit, KeyTalk, and enterprise platforms, see [Why certctl?](docs/why-certctl.md)
+
+## Who Is This For
+
+**Platform engineering and DevOps teams** managing 10–500+ certificates across mixed infrastructure who need automated renewal, deployment, and a single dashboard for visibility. If you're currently running certbot cron jobs, manually renewing certs, or stitching together scripts — certctl replaces all of that.
+
+**Security and compliance teams** who need an immutable audit trail, certificate ownership tracking, policy enforcement, and evidence for SOC 2, PCI-DSS 4.0, or NIST SP 800-57 audits.
+
+**Small teams without enterprise budgets** who need the lifecycle automation that Venafi and Keyfactor provide but can't justify six-figure licensing for a 50-server environment.
 
 ## What It Does
 
-certctl gives you a single pane of glass for every TLS certificate in your organization:
+- **Certificates renew and deploy themselves.** The scheduler monitors expiration, creates renewal jobs, issues certificates through your CA, and deploys them to target servers — all without human intervention. ACME ARI (RFC 9702) lets your CA tell certctl exactly when to renew.
 
-- **Web dashboard** — 22 operational pages: certificate inventory, deployment timeline with TLS verification, bulk operations (renew/revoke/reassign), discovery triage, network scan management, approval workflows, audit trail with CSV/JSON export, agent fleet overview with OS/arch grouping, short-lived credential monitoring, digest email preview
-- **REST API** — 99 endpoints under `/api/v1/` + `/.well-known/est/` for complete automation, with sparse fields, sort, cursor pagination, and time-range filters
-- **Agents** — generate private keys locally (ECDSA P-256), discover existing certs on disk (PEM/DER), submit CSRs only (private keys never leave your servers)
-- **Network scanner** — discovers certificates on TLS endpoints across CIDR ranges without requiring agents, concurrent scanning with configurable timeouts
-- **Certificate export** — PEM (JSON or file download) and PKCS#12 formats, with audit trail; private keys never included
-- **S/MIME + EKU support** — issue certificates with emailProtection, codeSigning, timeStamping, clientAuth EKUs; email SAN routing for S/MIME
-- **EST server** (RFC 7030) — device and WiFi certificate enrollment via industry-standard protocol
-- **Post-deployment verification** — agent-side TLS probe confirms the target serves the correct certificate by SHA-256 fingerprint match
-- **Approval workflows** — require human sign-off on renewals before deployment
-- **Background scheduler** — 7 automated loops: renewal checks, job processing, agent health, notifications, short-lived cert expiry, network scanning, and scheduled certificate digest emails
-- **ACME Renewal Information (ARI, RFC 9702)** — CA-directed renewal timing; certctl asks the CA when to renew instead of using fixed thresholds
-- **Scheduled certificate digest emails** — HTML digest with certificate stats, expiration timeline, and job health; optional daily briefing via SMTP
-- **Helm chart** — Production-ready Kubernetes deployment with server, PostgreSQL, and agent DaemonSet
+- **You see everything in one place.** A 25-page operational dashboard shows every certificate across every server: status, ownership, expiration timeline, deployment history with TLS verification, discovery triage, and real-time agent fleet health. Bulk operations (renew, revoke, reassign) work across selections.
 
-For the full capability breakdown — revocation infrastructure, policy engine, observability, EST enrollment, and more — see the [Feature Inventory](docs/features.md).
+- **Private keys never leave your servers.** Agents generate ECDSA P-256 keys locally and submit only the CSR. The control plane never touches private keys. Post-deployment TLS verification confirms the right certificate is actually being served.
+
+- **Discover what you don't know about.** Agents scan filesystems for existing PEM/DER certificates. The network scanner probes TLS endpoints across CIDR ranges without requiring agents. Both feed into a triage workflow where you claim, dismiss, or import discovered certificates.
+
+- **Everything is auditable.** Immutable append-only audit trail records every lifecycle action, every API call, and every approval decision. Certificate digest emails deliver daily briefings. Prometheus metrics endpoint for Grafana dashboards.
+
+- **Multiple interfaces for different workflows.** REST API (97 endpoints) for automation, CLI for scripting, MCP server for AI assistants (Claude, Cursor, Windsurf), EST server (RFC 7030) for device enrollment, Helm chart for Kubernetes, and the web dashboard for day-to-day operations.
+
+For the full capability breakdown — revocation infrastructure (CRL + OCSP), policy engine, certificate profiles, S/MIME support, approval workflows, and more — see the [Feature Inventory](docs/features.md).
 
 ## Supported Integrations
 
@@ -100,8 +97,9 @@ For the full capability breakdown — revocation infrastructure, policy engine,
 | HAProxy | Implemented | `HAProxy` |
 | Traefik | Implemented | `Traefik` |
 | Caddy | Implemented | `Caddy` |
+| Envoy | Implemented | `Envoy` |
+| Microsoft IIS | Implemented (local + WinRM) | `IIS` |
 | F5 BIG-IP | Interface only | `F5` |
-| Microsoft IIS | Interface only | `IIS` |
 
 ### Notifiers
 | Notifier | Status | Type |
@@ -131,10 +129,10 @@ All connectors are pluggable — build your own by implementing the [connector i
 <tr>
 <td><a href="docs/screenshots/v2-policies.png"><img src="docs/screenshots/v2-policies.png" width="270" alt="Policies"></a><br><b>Policies</b><br><sub>Ownership, lifetime, renewal rules</sub></td>
 <td><a href="docs/screenshots/v2-profiles.png"><img src="docs/screenshots/v2-profiles.png" width="270" alt="Profiles"></a><br><b>Profiles</b><br><sub>Key types, max TTL, crypto constraints</sub></td>
-<td><a href="docs/screenshots/v2-issuers.png"><img src="docs/screenshots/v2-issuers.png" width="270" alt="Issuers"></a><br><b>Issuers</b><br><sub>Local CA, ACME, step-ca connectors</sub></td>
+<td><a href="docs/screenshots/v2-issuers.png"><img src="docs/screenshots/v2-issuers.png" width="270" alt="Issuers"></a><br><b>Issuers</b><br><sub>Local CA, ACME, step-ca, Vault PKI, DigiCert</sub></td>
 </tr>
 <tr>
-<td><a href="docs/screenshots/v2-targets.png"><img src="docs/screenshots/v2-targets.png" width="270" alt="Targets"></a><br><b>Targets</b><br><sub>NGINX, Apache, HAProxy, Traefik, Caddy deployment</sub></td>
+<td><a href="docs/screenshots/v2-targets.png"><img src="docs/screenshots/v2-targets.png" width="270" alt="Targets"></a><br><b>Targets</b><br><sub>NGINX, Apache, HAProxy, Traefik, Caddy, IIS deployment</sub></td>
 <td><a href="docs/screenshots/v2-owners.png"><img src="docs/screenshots/v2-owners.png" width="270" alt="Owners"></a><br><b>Owners</b><br><sub>Cert ownership with team assignment</sub></td>
 <td><a href="docs/screenshots/v2-teams.png"><img src="docs/screenshots/v2-teams.png" width="270" alt="Teams"></a><br><b>Teams</b><br><sub>Org grouping for notification routing</sub></td>
 </tr>
@@ -145,17 +143,8 @@ All connectors are pluggable — build your own by implementing the [connector i
 </tr>
 </table>
 
-> **22 operational GUI pages** covering the full certificate lifecycle: dashboard, certificates (list + detail with EKU badges, deployment timeline, TLS verification status), agents, fleet overview, jobs (with approval workflow), notifications, policies, profiles, issuers, targets (wizard with NGINX/Apache/HAProxy/Traefik/Caddy/F5/IIS), owners, teams, agent groups, audit trail, short-lived credentials, discovery triage, and network scan management.
-
 ## Quick Start
 
-### Docker Pull
-
-```bash
-docker pull shankar0123.docker.scarf.sh/certctl-server
-docker pull shankar0123.docker.scarf.sh/certctl-agent
-```
-
 ### Docker Compose (Recommended)
 
 ```bash
@@ -166,15 +155,14 @@ docker compose -f deploy/docker-compose.yml up -d --build
 
 Wait ~30 seconds, then open **http://localhost:8443** in your browser.
 
-The dashboard comes pre-loaded with 35 demo certificates across 5 issuers, 8 agents, 90 days of job history, discovery scan data, and network scan targets — a realistic snapshot of a certificate inventory that looks like it's been running for months.
+The dashboard comes pre-loaded with 32 demo certificates across 7 issuers, 8 agents, 180 days of job history, discovery scan data, and network scan targets — a realistic snapshot of a certificate inventory that looks like it's been running for months.
 
-Verify the API:
 ```bash
 curl http://localhost:8443/health
 # {"status":"healthy"}
 
 curl -s http://localhost:8443/api/v1/certificates | jq '.total'
-# 35
+# 32
 ```
 
 ### Agent Install (One-Liner)
@@ -185,32 +173,30 @@ curl -sSL https://raw.githubusercontent.com/shankar0123/certctl/master/install-a
 
 Detects your OS and architecture, downloads the binary, configures systemd (Linux) or launchd (macOS), and starts the agent. See [install-agent.sh](install-agent.sh) for details.
 
-### Manual Build
+### Docker Pull
 
 ```bash
-# Prerequisites: Go 1.25+, PostgreSQL 16+, Docker (for testcontainers-go)
-go mod download
-make build
-
-# Set up database
-export CERTCTL_DATABASE_URL="postgres://certctl:certctl@localhost:5432/certctl?sslmode=disable"
-export CERTCTL_AUTH_TYPE=none
-make migrate-up
-
-# Start server
-./bin/server
-
-# Start agent (separate terminal)
-export CERTCTL_SERVER_URL=http://localhost:8443
-export CERTCTL_API_KEY=change-me-in-production
-export CERTCTL_AGENT_NAME=local-agent
-export CERTCTL_AGENT_ID=agent-local-01
-./bin/agent --agent-id=agent-local-01
+docker pull shankar0123.docker.scarf.sh/certctl-server
+docker pull shankar0123.docker.scarf.sh/certctl-agent
 ```
 
+## Examples
+
+Pick the scenario closest to your setup and have it running in 2 minutes.
+
+| Example | Scenario |
+|---------|----------|
+| [`examples/acme-nginx/`](examples/acme-nginx/) | Let's Encrypt + NGINX, HTTP-01 challenges |
+| [`examples/acme-wildcard-dns01/`](examples/acme-wildcard-dns01/) | Wildcard certs via DNS-01 (Cloudflare hook included) |
+| [`examples/private-ca-traefik/`](examples/private-ca-traefik/) | Local CA (self-signed or sub-CA) + Traefik file provider |
+| [`examples/step-ca-haproxy/`](examples/step-ca-haproxy/) | Smallstep step-ca + HAProxy combined PEM |
+| [`examples/multi-issuer/`](examples/multi-issuer/) | ACME for public + Local CA for internal, one dashboard |
+
+Each directory contains a `docker-compose.yml` and a `README.md` explaining the scenario, prerequisites, and customization.
+
 ## Architecture
 
-**Control plane** (Go 1.25 net/http) → **PostgreSQL 16** (21 tables, TEXT primary keys) → **Agents** (key generation, CSR submission, cert deployment). Background scheduler runs 7 loops: renewal checks (1h), job processing (30s), agent health (2m), notifications (1m), short-lived cert expiry (30s), network scanning (6h), certificate digest (24h). See [Architecture Guide](docs/architecture.md) for full system diagrams and data flow.
+**Control plane** (Go 1.25 net/http) → **PostgreSQL 16** (21 tables, TEXT primary keys) → **Agents** (key generation, CSR submission, cert deployment). For Windows servers without a local agent, a proxy agent in the same network zone handles deployment via WinRM. Background scheduler runs 7 loops: renewal checks (1h), job processing (30s), agent health (2m), notifications (1m), short-lived cert expiry (30s), network scanning (6h), certificate digest (24h). See [Architecture Guide](docs/architecture.md) for full system diagrams and data flow.
 
 ### Key Design Decisions
 
@@ -219,206 +205,23 @@ export CERTCTL_AGENT_ID=agent-local-01
 - **Handler → Service → Repository layering.** Handlers define their own service interfaces for clean dependency inversion. No global service singletons.
 - **Idempotent migrations.** All schema uses `IF NOT EXISTS` and seed data uses `ON CONFLICT (id) DO NOTHING`, safe for repeated execution.
 
-PostgreSQL 16 with 21 tables covering certificates, versions, policies, issuers, targets, agents, jobs, teams, owners, profiles, agent groups, revocations, discovery, network scans, and audit events. See the [Architecture Guide](docs/architecture.md) for the full schema.
+## Documentation
 
-## Configuration
-
-All environment variables use the `CERTCTL_` prefix. Full reference below (39 variables across server, agent, and connector config).
-
-### Server — Core
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_SERVER_HOST` | `127.0.0.1` | Server bind address |
-| `CERTCTL_SERVER_PORT` | `8080` | Server listen port (1–65535) |
-| `CERTCTL_DATABASE_URL` | `postgres://localhost/certctl` | PostgreSQL connection string (required) |
-| `CERTCTL_DATABASE_MAX_CONNS` | `25` | PostgreSQL connection pool size (min 1) |
-| `CERTCTL_DATABASE_MIGRATIONS_PATH` | `./migrations` | Path to migration SQL files |
-| `CERTCTL_MAX_BODY_SIZE` | `1048576` | Max HTTP request body in bytes (default 1MB) |
-| `CERTCTL_LOG_LEVEL` | `info` | Log verbosity: `debug`, `info`, `warn`, `error` |
-| `CERTCTL_LOG_FORMAT` | `json` | Log format: `json` (structured) or `text` (human-readable) |
-
-### Server — Auth, CORS, Rate Limiting
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_AUTH_TYPE` | `api-key` | Auth mode: `api-key`, `jwt`, or `none` (demo only) |
-| `CERTCTL_AUTH_SECRET` | — | Required for `api-key` and `jwt` auth types |
-| `CERTCTL_CORS_ORIGINS` | *(empty = deny all)* | Comma-separated allowed origins, or `*` for dev |
-| `CERTCTL_RATE_LIMIT_ENABLED` | `true` | Enable token bucket rate limiting |
-| `CERTCTL_RATE_LIMIT_RPS` | `50` | Requests per second per client |
-| `CERTCTL_RATE_LIMIT_BURST` | `100` | Max burst size |
-| `CERTCTL_KEYGEN_MODE` | `agent` | Key generation: `agent` (production) or `server` (demo only) |
-
-### Server — Scheduler
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_SCHEDULER_RENEWAL_CHECK_INTERVAL` | `1h` | How often to check expiring certs (min 1m) |
-| `CERTCTL_SCHEDULER_JOB_PROCESSOR_INTERVAL` | `30s` | How often to process pending jobs (min 1s) |
-| `CERTCTL_SCHEDULER_AGENT_HEALTH_CHECK_INTERVAL` | `2m` | Agent heartbeat check frequency (min 1s) |
-| `CERTCTL_SCHEDULER_NOTIFICATION_PROCESS_INTERVAL` | `1m` | Notification send frequency (min 1s) |
-
-### Server — Sub-CA Mode
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_CA_CERT_PATH` | — | PEM-encoded CA certificate for sub-CA mode |
-| `CERTCTL_CA_KEY_PATH` | — | PEM-encoded CA private key (RSA, ECDSA, PKCS#8) |
-
-### Server — Feature Flags
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_EST_ENABLED` | `false` | Enable RFC 7030 EST enrollment endpoints |
-| `CERTCTL_EST_ISSUER_ID` | `iss-local` | Which issuer processes EST enrollments |
-| `CERTCTL_EST_PROFILE_ID` | — | Constrain EST to a specific certificate profile |
-| `CERTCTL_NETWORK_SCAN_ENABLED` | `false` | Enable server-side TLS network scanning |
-| `CERTCTL_NETWORK_SCAN_INTERVAL` | `6h` | How often scheduled scans run |
-| `CERTCTL_VERIFY_DEPLOYMENT` | `true` | TLS verification after certificate deployment |
-| `CERTCTL_VERIFY_TIMEOUT` | `10s` | TLS probe timeout |
-| `CERTCTL_VERIFY_DELAY` | `2s` | Delay before verification probe |
-
-### Server — Notification Connectors
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_SLACK_WEBHOOK_URL` | — | Slack incoming webhook URL (enables Slack) |
-| `CERTCTL_SLACK_CHANNEL` | — | Override default webhook channel |
-| `CERTCTL_SLACK_USERNAME` | `certctl` | Bot display name |
-| `CERTCTL_TEAMS_WEBHOOK_URL` | — | Microsoft Teams webhook URL (enables Teams) |
-| `CERTCTL_PAGERDUTY_ROUTING_KEY` | — | PagerDuty Events API v2 key (enables PagerDuty) |
-| `CERTCTL_PAGERDUTY_SEVERITY` | `warning` | Event severity: `info`, `warning`, `error`, `critical` |
-| `CERTCTL_OPSGENIE_API_KEY` | — | OpsGenie Alert API key (enables OpsGenie) |
-| `CERTCTL_OPSGENIE_PRIORITY` | `P3` | Alert priority: `P1`–`P5` |
-
-### Agent
-
-| Variable | Default | Description |
-|----------|---------|-------------|
-| `CERTCTL_SERVER_URL` | `http://localhost:8080` | Control plane URL |
-| `CERTCTL_API_KEY` | — | Agent API key for authentication |
-| `CERTCTL_AGENT_ID` | — | Registered agent ID (required) |
-| `CERTCTL_KEY_DIR` | `/var/lib/certctl/keys` | Private key storage directory (0600 perms) |
-| `CERTCTL_DISCOVERY_DIRS` | — | Directories to scan for existing certs (comma-separated) |
-
-Docker Compose overrides for the demo stack are in `deploy/docker-compose.yml`.
-
-## Development
-
-```bash
-# Install dev tools (golangci-lint, migrate CLI, air)
-make install-tools
-
-# Run tests
-make test
-
-# Run tests with race detection (same as CI)
-go test -race ./internal/service/... ./internal/api/handler/... ./internal/api/middleware/... ./internal/scheduler/... ./internal/connector/... ./internal/domain/... ./internal/validation/...
-
-# Run with coverage
-make test-coverage
-
-# Lint (runs golangci-lint with project config)
-make lint
-
-# Vulnerability scan
-govulncheck ./...
-
-# Format
-make fmt
-```
-
-### CI Pipeline
-
-Every push and PR runs: `go vet`, `go test -race` (race detection), `golangci-lint` (11 linters including gosec and bodyclose), `govulncheck` (dependency CVE scanning), and per-layer coverage thresholds (service 60%, handler 60%, domain 40%, middleware 50%). Frontend CI runs TypeScript type checking, Vitest tests, and Vite production build. See `.github/workflows/ci.yml` for details.
-
-### Docker Compose
-
-```bash
-make docker-up          # Start stack (server + postgres + agent)
-make docker-down        # Stop stack
-make docker-logs-server # Server logs
-make docker-logs-agent  # Agent logs
-make docker-clean       # Stop + remove volumes
-```
-
-## Security
-
-### Private Key Management
-- **Agent keygen mode (default)**: Agents generate ECDSA P-256 keys locally and store them with 0600 permissions in `CERTCTL_KEY_DIR` (default `/var/lib/certctl/keys`). Only the CSR (public key) is sent to the control plane. Private keys never leave agent infrastructure.
-- **Server keygen mode (demo only)**: Set `CERTCTL_KEYGEN_MODE=server` for development/demo with Local CA. The control plane generates RSA-2048 keys server-side. A log warning is emitted at startup.
-
-### Authentication
-- Agent-to-server: API key (registered at agent creation)
-- API key and JWT auth types supported; `none` for demo/development
-- Auth type and secret configured via `CERTCTL_AUTH_TYPE` and `CERTCTL_AUTH_SECRET`
-
-### CORS
-- **Deny-by-default**: Empty `CERTCTL_CORS_ORIGINS` blocks all cross-origin requests. Operators must explicitly list allowed origins (comma-separated) or set `*` for development.
-
-### Input Validation
-- Shell command injection prevention on all connector scripts (strict character whitelist, no metacharacters)
-- RFC 1123 domain name validation, base64url ACME token validation
-- SSRF protection in network scanner (loopback, link-local, multicast, broadcast ranges filtered)
-
-### Concurrency Safety
-- Scheduler loops protected by `sync/atomic.Bool` idempotency guards — duplicate ticks are skipped
-- Graceful shutdown waits up to 30 seconds for in-flight work before database close
-
-### Audit Trail
-- Immutable append-only log in PostgreSQL (`audit_events` table)
-- Every lifecycle action attributed to an actor with timestamp and resource reference
-- No update or delete operations on audit records
-- Every API call recorded to audit trail with method, path, actor, SHA-256 body hash, response status, and latency
-
-## API Overview
-
-99 endpoints under `/api/v1/` + `/.well-known/est/`, all returning JSON. List endpoints support pagination, sparse field selection (`?fields=`), sort (`?sort=-notAfter`), time-range filters, and cursor-based pagination. Full request/response schemas in the [OpenAPI 3.1 spec](api/openapi.yaml).
-
-### Key Endpoints
-```
-# Certificate lifecycle
-GET    /api/v1/certificates              List (filter, sort, cursor, sparse fields)
-POST   /api/v1/certificates/{id}/renew   Trigger renewal → 202 Accepted
-POST   /api/v1/certificates/{id}/revoke  Revoke with RFC 5280 reason code
-GET    /api/v1/certificates/{id}/export/pem    Export PEM (JSON or file download)
-POST   /api/v1/certificates/{id}/export/pkcs12 Export PKCS#12 bundle (no private key)
-GET    /api/v1/crl/{issuer_id}           DER-encoded X.509 CRL
-GET    /api/v1/ocsp/{issuer_id}/{serial} OCSP responder (good/revoked/unknown)
-
-# Agent operations
-POST   /api/v1/agents/{id}/csr           Submit CSR for issuance
-GET    /api/v1/agents/{id}/work          Poll for pending deployment jobs
-POST   /api/v1/agents/{id}/discoveries   Submit certificate discovery scan results
-
-# Discovery & network scanning
-GET    /api/v1/discovered-certificates   List discovered certs (?agent_id, ?status)
-POST   /api/v1/discovered-certificates/{id}/claim  Link to managed cert
-POST   /api/v1/network-scan-targets/{id}/scan      Trigger immediate TLS scan
-
-# Jobs & approval
-POST   /api/v1/jobs/{id}/approve         Approve interactive renewal
-POST   /api/v1/jobs/{id}/reject          Reject interactive renewal
-
-# Post-deployment verification
-POST   /api/v1/jobs/{id}/verify          Submit TLS verification result
-GET    /api/v1/jobs/{id}/verification    Get verification status
-
-# Observability
-GET    /api/v1/metrics/prometheus         Prometheus exposition format
-GET    /api/v1/stats/summary             Dashboard summary
-
-# Digest emails (scheduled briefing)
-GET    /api/v1/digest/preview            HTML email preview
-POST   /api/v1/digest/send               Send digest immediately
-
-# EST enrollment (RFC 7030)
-POST   /.well-known/est/simpleenroll     Device certificate enrollment
-GET    /.well-known/est/cacerts          CA certificate chain (PKCS#7)
-```
-
-Full CRUD is available for certificates, agents, issuers, targets, teams, owners, policies, profiles, agent groups, notifications, and audit events. See the [OpenAPI spec](api/openapi.yaml) or [Feature Inventory](docs/features.md) for the complete endpoint reference.
+| Guide | Description |
+|-------|-------------|
+| [Why certctl?](docs/why-certctl.md) | How certctl compares to open-source and enterprise certificate management platforms |
+| [Concepts](docs/concepts.md) | TLS certificates explained from scratch — for beginners who know nothing about certs |
+| [Quick Start](docs/quickstart.md) | Extended quickstart — dashboard, API, CLI, discovery, stakeholder demo flow |
+| [Advanced Demo](docs/demo-advanced.md) | Issue a certificate end-to-end with technical deep-dives |
+| [Architecture](docs/architecture.md) | System design, data flow diagrams, security model |
+| [Feature Inventory](docs/features.md) | Complete reference of all V2 capabilities, API endpoints, and configuration |
+| [Configuration Reference](docs/features.md) | All 39 environment variables across server, agent, and connector config |
+| [Connectors](docs/connectors.md) | Build custom issuer, target, and notifier connectors |
+| [Compliance Mapping](docs/compliance.md) | SOC 2 Type II, PCI-DSS 4.0, NIST SP 800-57 alignment guides |
+| [Migrate from Certbot](docs/migrate-from-certbot.md) | Step-by-step migration from Certbot/Let's Encrypt cron jobs |
+| [Migrate from acme.sh](docs/migrate-from-acmesh.md) | Migration guide for acme.sh users with DNS-01 scripts |
+| [certctl for cert-manager Users](docs/certctl-for-cert-manager-users.md) | Using certctl alongside cert-manager for non-Kubernetes infrastructure |
+| [OpenAPI 3.1 Spec](api/openapi.yaml) | 97 operations, full request/response schemas |
 
 ## CLI
 
@@ -430,38 +233,26 @@ go install github.com/shankar0123/certctl/cmd/cli@latest
 export CERTCTL_SERVER_URL=http://localhost:8443
 export CERTCTL_API_KEY=your-api-key
 
-# Certificate commands
+# Usage
 certctl-cli certs list                    # List all certificates
-certctl-cli certs get mc-api-prod         # Get certificate details
 certctl-cli certs renew mc-api-prod       # Trigger renewal
 certctl-cli certs revoke mc-api-prod --reason keyCompromise
-
-# Agent and job commands
 certctl-cli agents list                   # List registered agents
 certctl-cli jobs list                     # List jobs
-certctl-cli jobs cancel job-123           # Cancel a pending job
-
-# Operations
 certctl-cli status                        # Server health + summary stats
 certctl-cli import certs.pem              # Bulk import from PEM file
-
-# Output formats
 certctl-cli certs list --format json      # JSON output (default: table)
 ```
 
 ## MCP Server (AI Integration)
 
-certctl ships a standalone MCP (Model Context Protocol) server that exposes all 78 API endpoints as tools for AI assistants — Claude, Cursor, Windsurf, OpenClaw, VS Code Copilot, and any MCP-compatible client.
+certctl ships a standalone MCP (Model Context Protocol) server that exposes all API endpoints as tools for AI assistants — Claude, Cursor, Windsurf, OpenClaw, VS Code Copilot, and any MCP-compatible client.
 
 ```bash
-# Install
+# Install and run
 go install github.com/shankar0123/certctl/cmd/mcp-server@latest
-
-# Configure
 export CERTCTL_SERVER_URL=http://localhost:8443
 export CERTCTL_API_KEY=your-api-key
-
-# Run (stdio transport — add to your AI client config)
 mcp-server
 ```
 
@@ -480,70 +271,44 @@ mcp-server
 }
 ```
 
+## Security
+
+certctl is designed with a security-first architecture. Agents generate ECDSA P-256 keys locally — private keys never touch the control plane. API key auth is enforced by default with SHA-256 hashing and constant-time comparison. CORS is deny-by-default. All connector scripts are validated against shell injection. The network scanner filters reserved IP ranges (SSRF protection). Scheduler loops use atomic idempotency guards. Every API call is recorded to an immutable audit trail with actor attribution, SHA-256 body hash, and latency tracking. See the [Architecture Guide](docs/architecture.md) for the full security model.
+
+## Development
+
+```bash
+make build              # Build server + agent binaries
+make test               # Run tests
+make lint               # golangci-lint (11 linters)
+govulncheck ./...       # Vulnerability scan
+make docker-up          # Start Docker Compose stack
+```
+
+CI runs on every push: `go vet`, `go test -race`, `golangci-lint`, `govulncheck`, and per-layer coverage thresholds (service 55%, handler 60%, domain 40%, middleware 30%). Frontend CI runs TypeScript type checking, Vitest tests, and Vite production build.
+
 ## Roadmap
 
-### V1 (v1.0.0)
+### V1 (v1.0.0) — Shipped
 Core lifecycle management — Local CA + ACME v2 issuers, NGINX target connector, agent-side key generation, API auth + rate limiting, React dashboard, CI pipeline with coverage gates, Docker images on GHCR.
 
-### V2: Operational Maturity
+### V2: Operational Maturity — Shipped
+30+ milestones, 1,536+ tests. Sub-CA mode, ACME DNS-01/DNS-PERSIST-01, step-ca, Vault PKI, DigiCert CertCentral, OpenSSL/Custom CA issuers. NGINX, Apache, HAProxy, Traefik, Caddy, Envoy, IIS targets. RFC 5280 revocation with CRL + OCSP. Certificate profiles, ownership tracking, approval workflows. Filesystem and network certificate discovery. Prometheus metrics, dashboard charts, agent fleet overview. EST server (RFC 7030), ACME ARI (RFC 9702), certificate export, S/MIME support, Helm chart, MCP server, CLI, scheduled digest emails. Slack, Teams, PagerDuty, OpsGenie, SMTP notifications. Compliance mapping (SOC 2, PCI-DSS 4.0, NIST SP 800-57). See the [Feature Inventory](docs/features.md) for details.
 
-30 milestones complete, 1500+ tests. See the [Feature Inventory](docs/features.md) for details on every capability.
-
-**What shipped (all ✅):**
-
-- **Issuers** — Sub-CA mode (enterprise root chains), ACME DNS-01 + DNS-PERSIST-01 (wildcard certs, any DNS provider), step-ca (native /sign API), OpenSSL/Custom CA (script-based signing), ACME ARI (RFC 9702, CA-directed renewal timing)
-- **Revocation** — RFC 5280 reason codes, DER-encoded X.509 CRL, embedded OCSP responder, short-lived cert exemption
-- **Profiles + Ownership** — certificate profiles (key types, max TTL, crypto constraints), ownership tracking (owners + teams), dynamic agent groups, interactive renewal approval
-- **GUI Operations** — bulk renew/revoke/reassign, deployment timeline, inline policy editor, target wizard, audit export (CSV/JSON), short-lived credentials view
-- **Discovery** — filesystem scanning (PEM/DER) + network TLS scanning (CIDR ranges), triage workflow (claim/dismiss), network scan target management
-- **Observability** — Prometheus + JSON metrics, 5 stats API endpoints, dashboard charts (heatmap, trends, distribution), agent fleet overview, structured logging
-- **EST Server** (RFC 7030) — device/WiFi certificate enrollment, PKCS#7 wire format, configurable issuer + profile binding
-- **MCP Server** — 78 API operations as AI tools for Claude, Cursor, and any MCP-compatible client
-- **CLI** — 12 subcommands (list/get/renew/revoke certs, agents, jobs, import, status), JSON/table output
-- **Notifications** — Email (SMTP), Webhooks, Slack, Microsoft Teams, PagerDuty, OpsGenie connectors
-- **API Enhancements** — sparse fields, sort, time-range filters, cursor pagination, immutable API audit logging
-- **Compliance Mapping** — SOC 2 Type II, PCI-DSS 4.0, NIST SP 800-57 alignment guides
-
-- **Post-Deployment TLS Verification** — agent-side TLS probe confirms the target is serving the correct certificate by SHA-256 fingerprint match, verification status visible in deployment timeline
-- **Traefik + Caddy Targets** — Traefik (file provider, auto-reload) and Caddy (Admin API hot-reload or file-based), both in target wizard GUI
-- **Certificate Export** — PEM (JSON or file download) and PKCS#12 formats, private keys never included (agent-side only), audit trail, GUI export buttons
-- **S/MIME Support** — EKU-aware issuance (emailProtection, codeSigning, timeStamping), adaptive KeyUsage flags, email SAN routing, EKU badges in GUI
-- **ACME ARI (RFC 9702)** — CA-directed renewal timing: the CA tells certctl the optimal renewal window, gracefully degrading to fixed thresholds when ARI is unavailable
-- **Scheduled Certificate Digest** — HTML email digests with certificate stats, expiration timeline, job trends, and agent health; configurable daily/hourly/weekly briefings via SMTP
-- **Helm Chart** — Production-ready Kubernetes with server Deployment, PostgreSQL StatefulSet with PVC, Agent DaemonSet, security contexts, resource limits, optional Ingress
-
-**Coming in v2.1.0:**
-- Dynamic issuer and target configuration via GUI (no env var restarts)
-- Issuer catalog page (see all supported CAs, configure from dashboard)
-- First-run onboarding wizard
-- Turnkey deployment examples (ACME+NGINX, wildcard+DNS-01, private CA+Traefik, step-ca+HAProxy, multi-issuer)
-- Migration guides (Certbot, acme.sh, cert-manager complement)
-- One-line agent install script with cross-compiled binaries
+**Coming in v2.1.0:** Dynamic issuer and target configuration via GUI (no env var restarts), first-run onboarding wizard.
 
 ### V3: certctl Pro
-
-Team access controls, identity provider integration, enterprise deployment targets, compliance and risk scoring, advanced fleet operations, event-driven architecture, advanced search, real-time operational views.
+Team access controls and identity provider integration (OIDC/SSO). Role-based access control with profile-gating. Event-driven architecture (NATS) with real-time operational views. Advanced search DSL, compliance and risk scoring, bulk fleet operations.
 
 ### V4+: Cloud, Scale & Passive Discovery
 Passive network discovery (TLS listener), Kubernetes integration (cert-manager external issuer, Secrets target), cloud infrastructure targets (AWS ALB/ACM, Azure Key Vault), extended CA support (Google CAS, EJBCA, Sectigo), and platform-scale features (Terraform provider, multi-tenancy, HSM support).
 
-## Examples
-
-Turnkey Docker Compose configurations for common scenarios — pick the one closest to your setup and have it running in 2 minutes.
-
-| Example | Scenario |
-|---------|----------|
-| [`examples/acme-nginx/`](examples/acme-nginx/) | Let's Encrypt + NGINX, HTTP-01 challenges |
-| [`examples/acme-wildcard-dns01/`](examples/acme-wildcard-dns01/) | Wildcard certs via DNS-01 (Cloudflare hook included) |
-| [`examples/private-ca-traefik/`](examples/private-ca-traefik/) | Local CA (self-signed or sub-CA) + Traefik file provider |
-| [`examples/step-ca-haproxy/`](examples/step-ca-haproxy/) | Smallstep step-ca + HAProxy combined PEM |
-| [`examples/multi-issuer/`](examples/multi-issuer/) | ACME for public + Local CA for internal, one dashboard |
-
-Each directory contains a `docker-compose.yml` and a `README.md` explaining the scenario, prerequisites, and customization.
-
 ## License
 
 Certctl is licensed under the [Business Source License 1.1](LICENSE). The source code is publicly available and free to use, modify, and self-host. The one restriction: you may not offer certctl as a managed/hosted certificate management service to third parties. The BSL 1.1 license converts automatically to Apache 2.0 on March 1, 2033, providing perpetual freedom.
 
 For licensing inquiries: certctl@proton.me
 
+---
+
+If certctl solves a problem you have, [star the repo](https://github.com/shankar0123/certctl) to help others find it. Questions, bugs, or feature requests — [open an issue](https://github.com/shankar0123/certctl/issues).

api/openapi.yaml

@@ -2669,7 +2669,7 @@ components:
     # ─── Targets ─────────────────────────────────────────────────────
     TargetType:
       type: string
-      enum: [NGINX, Apache, HAProxy, F5, IIS]
+      enum: [NGINX, Apache, HAProxy, Traefik, Caddy, Envoy, IIS, F5]
 
     DeploymentTarget:
       type: object

cmd/agent/main.go

@@ -29,6 +29,7 @@ import (
 	"github.com/shankar0123/certctl/internal/connector/target"
 	"github.com/shankar0123/certctl/internal/connector/target/apache"
 	"github.com/shankar0123/certctl/internal/connector/target/caddy"
+	"github.com/shankar0123/certctl/internal/connector/target/envoy"
 	"github.com/shankar0123/certctl/internal/connector/target/f5"
 	"github.com/shankar0123/certctl/internal/connector/target/haproxy"
 	"github.com/shankar0123/certctl/internal/connector/target/iis"
@@ -592,7 +593,7 @@ func (a *Agent) createTargetConnector(targetType string, configJSON json.RawMess
 				return nil, fmt.Errorf("invalid IIS config: %w", err)
 			}
 		}
-		return iis.New(&cfg, a.logger), nil
+		return iis.New(&cfg, a.logger)
 
 	case "Traefik":
 		var cfg traefik.Config
@@ -612,6 +613,15 @@ func (a *Agent) createTargetConnector(targetType string, configJSON json.RawMess
 		}
 		return caddy.New(&cfg, a.logger), nil
 
+	case "Envoy":
+		var cfg envoy.Config
+		if len(configJSON) > 0 {
+			if err := json.Unmarshal(configJSON, &cfg); err != nil {
+				return nil, fmt.Errorf("invalid Envoy config: %w", err)
+			}
+		}
+		return envoy.New(&cfg, a.logger), nil
+
 	default:
 		return nil, fmt.Errorf("unsupported target type: %s", targetType)
 	}

cmd/server/main.go

@@ -112,6 +112,7 @@ func main() {
 		DNSPresentScript:       os.Getenv("CERTCTL_ACME_DNS_PRESENT_SCRIPT"),
 		DNSCleanUpScript:       os.Getenv("CERTCTL_ACME_DNS_CLEANUP_SCRIPT"),
 		DNSPersistIssuerDomain: os.Getenv("CERTCTL_ACME_DNS_PERSIST_ISSUER_DOMAIN"),
+		Insecure:               cfg.ACME.Insecure,
 	}, logger)
 	logger.Info("initialized ACME issuer connector")
 
@@ -119,6 +120,7 @@ func main() {
 	// Uses the native /sign API with JWK provisioner authentication.
 	stepcaConnector := stepcaissuer.New(&stepcaissuer.Config{
 		CAURL:               os.Getenv("CERTCTL_STEPCA_URL"),
+		RootCertPath:        os.Getenv("CERTCTL_STEPCA_ROOT_CERT"),
 		ProvisionerName:     os.Getenv("CERTCTL_STEPCA_PROVISIONER"),
 		ProvisionerKeyPath:  os.Getenv("CERTCTL_STEPCA_KEY_PATH"),
 		ProvisionerPassword: os.Getenv("CERTCTL_STEPCA_PASSWORD"),
@@ -261,6 +263,8 @@ func main() {
 	certificateService.SetRevocationSvc(revocationSvc)
 	certificateService.SetCAOperationsSvc(caOperationsSvc)
 	certificateService.SetTargetRepo(targetRepo)
+	certificateService.SetJobRepo(jobRepo)
+	certificateService.SetKeygenMode(cfg.Keygen.Mode)
 	renewalService := service.NewRenewalService(certificateRepo, jobRepo, renewalPolicyRepo, profileRepo, auditService, notificationService, issuerRegistry, cfg.Keygen.Mode)
 	renewalService.SetTargetRepo(targetRepo)
 	deploymentService := service.NewDeploymentService(jobRepo, targetRepo, agentRepo, certificateRepo, auditService, notificationService)
@@ -504,13 +508,28 @@ func main() {
 	if _, err := os.Stat(webDir + "/index.html"); err != nil {
 		webDir = "./web"
 	}
+	// Health/ready routes bypass the full middleware stack (no auth required).
+	// These are registered on the inner router without auth, but the outer
+	// middleware chain wraps everything. Route them directly to the inner router.
+	noAuthHandler := middleware.Chain(apiRouter,
+		middleware.RequestID,
+		structuredLogger,
+		middleware.Recovery,
+	)
+
 	if _, err := os.Stat(webDir + "/index.html"); err == nil {
 		fileServer := http.FileServer(http.Dir(webDir))
 		finalHandler = http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 			path := r.URL.Path
-			// API, health, and EST routes go to the API handler
-			if path == "/health" || path == "/ready" ||
-				(len(path) >= 8 && path[:8] == "/api/v1/") ||
+			// Health/ready and auth/info bypass auth middleware.
+			// Health/ready: Docker/K8s health probes don't carry Bearer tokens.
+			// auth/info: React app calls this before login to detect auth mode.
+			if path == "/health" || path == "/ready" || path == "/api/v1/auth/info" {
+				noAuthHandler.ServeHTTP(w, r)
+				return
+			}
+			// All other API and EST routes go through the full middleware stack (with auth)
+			if (len(path) >= 8 && path[:8] == "/api/v1/") ||
 				(len(path) >= 16 && path[:16] == "/.well-known/est") {
 				apiHandler.ServeHTTP(w, r)
 				return
@@ -525,7 +544,15 @@ func main() {
 		})
 		logger.Info("dashboard available at /", "web_dir", webDir)
 	} else {
-		finalHandler = apiHandler
+		// No dashboard: route health/auth-info without auth, everything else through full stack
+		finalHandler = http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			path := r.URL.Path
+			if path == "/health" || path == "/ready" || path == "/api/v1/auth/info" {
+				noAuthHandler.ServeHTTP(w, r)
+				return
+			}
+			apiHandler.ServeHTTP(w, r)
+		})
 		logger.Info("dashboard directory not found, serving API only")
 	}
 
@@ -534,9 +561,9 @@ func main() {
 	httpServer := &http.Server{
 		Addr:              addr,
 		Handler:           finalHandler,
-		ReadTimeout:       15 * time.Second,
+		ReadTimeout:       30 * time.Second,
 		ReadHeaderTimeout: 5 * time.Second,
-		WriteTimeout:      15 * time.Second,
+		WriteTimeout:      120 * time.Second, // Must accommodate ACME issuance (order + challenge + finalize)
 		IdleTimeout:       60 * time.Second,
 	}
 

deploy/docker-compose.test.yml

@@ -0,0 +1,309 @@
+# =============================================================================
+# certctl Testing Environment — Docker Compose
+# =============================================================================
+#
+# Spins up the full certctl platform with real CA backends for manual QA:
+#
+#   1. PostgreSQL 16        — database (clean, no demo data)
+#   2. certctl-server       — control plane API + web dashboard on :8443
+#   3. certctl-agent        — polls for work, deploys certs to NGINX
+#   4. step-ca              — private CA (JWK provisioner, auto-bootstraps)
+#   5. Pebble               — ACME test server (simulates Let's Encrypt)
+#   6. pebble-challtestsrv  — DNS/HTTP challenge test server for Pebble
+#   7. NGINX                — TLS target server on :8080 (HTTP) / :8444 (HTTPS)
+#
+# Usage:
+#   cd deploy
+#   docker compose -f docker-compose.test.yml up --build
+#
+# Dashboard:  http://localhost:8443
+# API key:    test-key-2026
+# NGINX:      https://localhost:8444 (self-signed placeholder until cert deployed)
+#
+# See docs/test-env.md for the full walkthrough.
+# =============================================================================
+
+services:
+
+  # ---------------------------------------------------------------------------
+  # Database
+  # ---------------------------------------------------------------------------
+  postgres:
+    image: postgres:16-alpine
+    container_name: certctl-test-postgres
+    environment:
+      POSTGRES_DB: certctl
+      POSTGRES_USER: certctl
+      POSTGRES_PASSWORD: testpass
+    volumes:
+      - test_postgres_data:/var/lib/postgresql/data
+      - ../migrations/000001_initial_schema.up.sql:/docker-entrypoint-initdb.d/001_schema.sql
+      - ../migrations/000002_agent_metadata.up.sql:/docker-entrypoint-initdb.d/002_agent_metadata.sql
+      - ../migrations/000003_certificate_profiles.up.sql:/docker-entrypoint-initdb.d/003_certificate_profiles.sql
+      - ../migrations/000004_agent_groups.up.sql:/docker-entrypoint-initdb.d/004_agent_groups.sql
+      - ../migrations/000005_revocation.up.sql:/docker-entrypoint-initdb.d/005_revocation.sql
+      - ../migrations/000006_discovery.up.sql:/docker-entrypoint-initdb.d/006_discovery.sql
+      - ../migrations/000007_network_discovery.up.sql:/docker-entrypoint-initdb.d/007_network_discovery.sql
+      - ../migrations/000008_verification.up.sql:/docker-entrypoint-initdb.d/008_verification.sql
+      - ../migrations/seed.sql:/docker-entrypoint-initdb.d/010_seed.sql
+      - ../migrations/seed_test.sql:/docker-entrypoint-initdb.d/015_seed_test.sql
+      # No seed_demo.sql — start with a clean database for real testing
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.2
+    ports:
+      - "5432:5432"
+    healthcheck:
+      test: ["CMD-SHELL", "pg_isready -U certctl -d certctl"]
+      interval: 5s
+      timeout: 5s
+      retries: 5
+    restart: unless-stopped
+
+  # ---------------------------------------------------------------------------
+  # Pebble — ACME test server (simulates Let's Encrypt)
+  # ---------------------------------------------------------------------------
+  # Pebble is the official ACME test server from Let's Encrypt (RFC 8555).
+  # It validates challenges via the companion challtestsrv.
+  # Root CA cert available at https://pebble:15000/roots/0 (management API).
+  pebble-challtestsrv:
+    image: ghcr.io/letsencrypt/pebble-challtestsrv:latest
+    container_name: certctl-test-challtestsrv
+    # ENTRYPOINT is /app (the binary). command: provides only the FLAGS.
+    # Matches the official Pebble docker-compose format.
+    # -doh "" disables DoH (default :8443 would conflict with certctl server).
+    # defaultIPv4 must point to the certctl-server (10.30.50.6) because that's where
+    # the ACME HTTP-01 challenge server runs (port 80 inside the container).
+    # Pebble resolves domains via challtestsrv, then connects to this IP to validate.
+    command: -defaultIPv4 10.30.50.6 -defaultIPv6 "" -doh ""
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.3
+    restart: unless-stopped
+
+  pebble:
+    image: ghcr.io/letsencrypt/pebble:latest
+    container_name: certctl-test-pebble
+    depends_on:
+      - pebble-challtestsrv
+    environment:
+      PEBBLE_VA_NOSLEEP: 1
+      PEBBLE_VA_ALWAYS_VALID: 0
+    # ENTRYPOINT is /app (the binary). command: provides only the FLAGS.
+    command:
+      - -config
+      - /test/config/pebble-config.json
+      - -dnsserver
+      - "10.30.50.3:8053"
+      - -strict
+    volumes:
+      - ./test/pebble-config.json:/test/config/pebble-config.json:ro
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.4
+    restart: unless-stopped
+
+  # ---------------------------------------------------------------------------
+  # step-ca — Private CA (Smallstep)
+  # ---------------------------------------------------------------------------
+  # Auto-bootstraps on first run: generates root CA + JWK provisioner "admin".
+  # Root cert: /home/step/certs/root_ca.crt (inside stepca_data volume)
+  # Provisioner key: /home/step/secrets/provisioner_key (encrypted JWK)
+  step-ca:
+    image: smallstep/step-ca:latest
+    container_name: certctl-test-stepca
+    environment:
+      DOCKER_STEPCA_INIT_NAME: "certctl-test-ca"
+      DOCKER_STEPCA_INIT_DNS_NAMES: "step-ca,localhost"
+      DOCKER_STEPCA_INIT_PROVISIONER_NAME: "admin"
+      DOCKER_STEPCA_INIT_PASSWORD: "password123"
+      DOCKER_STEPCA_INIT_ADDRESS: ":9000"
+    volumes:
+      - stepca_data:/home/step
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.5
+    healthcheck:
+      test: ["CMD", "curl", "-fk", "https://localhost:9000/health"]
+      interval: 10s
+      timeout: 5s
+      start_period: 15s
+      retries: 10
+    restart: unless-stopped
+
+  # ---------------------------------------------------------------------------
+  # certctl Server (Control Plane)
+  # ---------------------------------------------------------------------------
+  # Connects to PostgreSQL, Pebble (ACME), step-ca, and Local CA.
+  #
+  # TLS trust problem: Pebble and step-ca use self-signed root CAs that
+  # aren't in Alpine's trust store. The ACME and step-ca connectors use
+  # Go's default http.Client (no InsecureSkipVerify), so they need the
+  # CA certs in the system trust store.
+  #
+  # Solution: setup-trust.sh runs as root, fetches Pebble CA from its
+  # management API, copies step-ca root cert from the shared volume,
+  # runs update-ca-certificates, then execs the server binary.
+  certctl-server:
+    build:
+      context: ..
+      dockerfile: Dockerfile
+    container_name: certctl-test-server
+    depends_on:
+      postgres:
+        condition: service_healthy
+      pebble:
+        condition: service_started
+      step-ca:
+        condition: service_healthy
+    # Run as root so update-ca-certificates can write to /etc/ssl/certs.
+    # Container isolation provides the security boundary.
+    user: "0:0"
+    entrypoint: ["/bin/sh", "/app/setup-trust.sh"]
+    environment:
+      # Database
+      CERTCTL_DATABASE_URL: postgres://certctl:testpass@postgres:5432/certctl?sslmode=disable
+
+      # Server
+      CERTCTL_SERVER_HOST: 0.0.0.0
+      CERTCTL_SERVER_PORT: 8443
+      CERTCTL_LOG_LEVEL: debug
+
+      # Auth — API key required (production-like)
+      CERTCTL_AUTH_TYPE: api-key
+      CERTCTL_AUTH_SECRET: test-key-2026
+
+      # Key generation — agent-side (production-like)
+      CERTCTL_KEYGEN_MODE: agent
+
+      # Local CA issuer (iss-local) — self-signed mode (no CA cert/key paths)
+      # This is the simplest issuer, always available.
+
+      # ACME issuer (iss-acme-staging) — pointed at Pebble
+      CERTCTL_ACME_DIRECTORY_URL: https://pebble:14000/dir
+      CERTCTL_ACME_EMAIL: test@certctl.dev
+      CERTCTL_ACME_CHALLENGE_TYPE: http-01
+      CERTCTL_ACME_INSECURE: "true"
+
+      # step-ca issuer (iss-stepca)
+      CERTCTL_STEPCA_URL: https://step-ca:9000
+      CERTCTL_STEPCA_ROOT_CERT: /stepca-data/certs/root_ca.crt
+      CERTCTL_STEPCA_PROVISIONER: admin
+      CERTCTL_STEPCA_PASSWORD: password123
+      CERTCTL_STEPCA_KEY_PATH: /stepca-data/secrets/provisioner_key
+
+      # EST server (RFC 7030) — uses Local CA by default
+      CERTCTL_EST_ENABLED: "true"
+      CERTCTL_EST_ISSUER_ID: iss-local
+
+      # Network scanning
+      CERTCTL_NETWORK_SCAN_ENABLED: "true"
+
+      # Post-deployment TLS verification
+      CERTCTL_VERIFY_DEPLOYMENT: "true"
+      CERTCTL_VERIFY_TIMEOUT: "10s"
+      CERTCTL_VERIFY_DELAY: "3s"
+    ports:
+      - "8443:8443"
+    volumes:
+      - ./test/setup-trust.sh:/app/setup-trust.sh:ro
+      # step-ca data volume (root cert at /certs/root_ca.crt, key at /secrets/provisioner_key)
+      - stepca_data:/stepca-data:ro
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.6
+    healthcheck:
+      # /health requires auth when CERTCTL_AUTH_TYPE=api-key, so include the Bearer token
+      test: ["CMD", "curl", "-f", "-H", "Authorization: Bearer test-key-2026", "http://localhost:8443/health"]
+      interval: 10s
+      timeout: 5s
+      start_period: 30s
+      retries: 10
+    restart: unless-stopped
+
+  # ---------------------------------------------------------------------------
+  # NGINX — TLS Target Server
+  # ---------------------------------------------------------------------------
+  # The agent deploys certificates here via the shared nginx_certs volume.
+  # nginx-entrypoint.sh generates a self-signed placeholder cert so NGINX
+  # can boot before the agent deploys a real cert.
+  #
+  # Ports: 8080 (HTTP) / 8444 (HTTPS) — offset to avoid conflict with server.
+  nginx:
+    image: nginx:alpine
+    container_name: certctl-test-nginx
+    entrypoint: ["/bin/sh", "/entrypoint.sh"]
+    volumes:
+      - ./test/nginx.conf:/etc/nginx/nginx.conf:ro
+      - ./test/nginx-entrypoint.sh:/entrypoint.sh:ro
+      - nginx_certs:/etc/nginx/certs
+    ports:
+      - "8080:80"
+      - "8444:443"
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.7
+    healthcheck:
+      test: ["CMD-SHELL", "curl -fk https://localhost/health || exit 1"]
+      interval: 10s
+      timeout: 5s
+      start_period: 15s
+      retries: 5
+    restart: unless-stopped
+
+  # ---------------------------------------------------------------------------
+  # certctl Agent
+  # ---------------------------------------------------------------------------
+  # Polls the server for work, generates ECDSA P-256 keys locally,
+  # deploys certs to NGINX via the shared volume, and discovers existing
+  # certs in the NGINX cert directory.
+  certctl-agent:
+    build:
+      context: ..
+      dockerfile: Dockerfile.agent
+    container_name: certctl-test-agent
+    depends_on:
+      certctl-server:
+        condition: service_healthy
+    environment:
+      CERTCTL_SERVER_URL: http://certctl-server:8443
+      CERTCTL_API_KEY: test-key-2026
+      CERTCTL_AGENT_NAME: test-agent-01
+      CERTCTL_AGENT_ID: agent-test-01
+      CERTCTL_KEYGEN_MODE: agent
+      CERTCTL_LOG_LEVEL: debug
+      CERTCTL_DISCOVERY_DIRS: /nginx-certs
+    volumes:
+      - agent_keys:/var/lib/certctl/keys
+      - nginx_certs:/nginx-certs
+    networks:
+      certctl-test:
+        ipv4_address: 10.30.50.8
+    restart: unless-stopped
+
+# =============================================================================
+# Network
+# =============================================================================
+# Static IPs are required because:
+# - Pebble needs to know the challtestsrv DNS server address (10.30.50.3)
+# - challtestsrv resolves all domains to certctl-server (10.30.50.6) for HTTP-01 challenges
+# - Avoids DNS race conditions during startup
+networks:
+  certctl-test:
+    driver: bridge
+    ipam:
+      config:
+        - subnet: 10.30.50.0/24
+
+# =============================================================================
+# Volumes
+# =============================================================================
+volumes:
+  test_postgres_data:
+    driver: local
+  stepca_data:
+    driver: local
+  agent_keys:
+    driver: local
+  nginx_certs:
+    driver: local

deploy/test/nginx-entrypoint.sh

@@ -0,0 +1,27 @@
+#!/bin/sh
+# Generate a self-signed placeholder certificate so NGINX can boot
+# before the certctl agent deploys a real certificate.
+# Once the agent deploys, it overwrites these files and reloads NGINX.
+
+CERT_DIR="/etc/nginx/certs"
+mkdir -p "$CERT_DIR"
+
+# Make cert directory world-writable so the certctl-agent container
+# (which shares this volume) can overwrite the placeholder certs.
+chmod 777 "$CERT_DIR"
+
+if [ ! -f "$CERT_DIR/cert.pem" ]; then
+    echo "Generating self-signed placeholder certificate..."
+    apk add --no-cache openssl > /dev/null 2>&1
+    openssl req -x509 -nodes -days 1 -newkey ec -pkeyopt ec_paramgen_curve:prime256v1 \
+        -keyout "$CERT_DIR/key.pem" \
+        -out "$CERT_DIR/cert.pem" \
+        -subj "/CN=placeholder.certctl.test" \
+        2>/dev/null
+    # Make placeholder certs writable by the agent container
+    chmod 666 "$CERT_DIR/cert.pem" "$CERT_DIR/key.pem"
+    echo "Placeholder certificate generated."
+fi
+
+# Start NGINX in foreground
+exec nginx -g "daemon off;"

deploy/test/nginx.conf

@@ -0,0 +1,42 @@
+# NGINX configuration for certctl test environment.
+# The agent deploys certificates to /etc/nginx/certs/ and reloads NGINX.
+# On startup, NGINX uses a self-signed placeholder so it can boot before any cert is deployed.
+
+# Generate a self-signed placeholder on container start (see entrypoint in compose).
+# Once the agent deploys a real cert, it overwrites these files and reloads.
+
+events {
+    worker_connections 1024;
+}
+
+http {
+    # HTTP → redirect to HTTPS (optional, for realism)
+    server {
+        listen 80;
+        server_name _;
+        return 301 https://$host$request_uri;
+    }
+
+    # HTTPS server — serves whatever cert the agent has deployed
+    server {
+        listen 443 ssl;
+        server_name _;
+
+        ssl_certificate     /etc/nginx/certs/cert.pem;
+        ssl_certificate_key /etc/nginx/certs/key.pem;
+
+        # Modern TLS settings
+        ssl_protocols TLSv1.2 TLSv1.3;
+        ssl_prefer_server_ciphers off;
+
+        location / {
+            default_type text/plain;
+            return 200 'certctl test environment — NGINX is serving TLS\n';
+        }
+
+        location /health {
+            default_type text/plain;
+            return 200 'ok\n';
+        }
+    }
+}

deploy/test/pebble-config.json

@@ -0,0 +1,16 @@
+{
+  "pebble": {
+    "listenAddress": "0.0.0.0:14000",
+    "managementListenAddress": "0.0.0.0:15000",
+    "certificate": "test/certs/localhost/cert.pem",
+    "privateKey": "test/certs/localhost/key.pem",
+    "httpPort": 80,
+    "tlsPort": 443,
+    "ocspResponderURL": "",
+    "externalAccountBindingRequired": false,
+    "retryAfter": {
+      "authz": 3,
+      "order": 5
+    }
+  }
+}

deploy/test/run-test.sh

@@ -0,0 +1,937 @@
+#!/usr/bin/env bash
+# =============================================================================
+# certctl End-to-End Test Script
+# =============================================================================
+#
+# Automates the full lifecycle test from docs/test-env.md:
+#   1. Bring up all 7 containers (build from source)
+#   2. Wait for every service to be healthy
+#   3. Verify pre-seeded data (agents, issuers, targets, profiles)
+#   4. Issue a certificate via Local CA → deploy to NGINX → verify TLS
+#   5. Issue a certificate via ACME/Pebble → verify
+#   6. Issue a certificate via step-ca → verify
+#   7. Test revocation + CRL
+#   8. Test discovery
+#   9. Test renewal (re-issue step-ca cert, check version history)
+#  10. EST enrollment (RFC 7030) — cacerts + simpleenroll
+#  11. S/MIME issuance — emailProtection EKU + adaptive KeyUsage
+#  12. API spot checks + print summary
+#
+# Usage:
+#   cd certctl/deploy
+#   ./test/run-test.sh          # full run (build + test)
+#   ./test/run-test.sh --no-build   # skip docker build, reuse existing containers
+#   ./test/run-test.sh --no-teardown # leave containers running after test
+#
+# Requirements: docker, curl, openssl, jq (or python3 for json parsing)
+# =============================================================================
+
+set -euo pipefail
+
+# ---------------------------------------------------------------------------
+# Config
+# ---------------------------------------------------------------------------
+COMPOSE_FILE="docker-compose.test.yml"
+API_URL="http://localhost:8443"
+API_KEY="test-key-2026"
+NGINX_TLS="localhost:8444"
+AUTH_HEADER="Authorization: Bearer ${API_KEY}"
+
+# Flags
+BUILD=true
+TEARDOWN=true
+for arg in "$@"; do
+  case "$arg" in
+    --no-build)    BUILD=false ;;
+    --no-teardown) TEARDOWN=false ;;
+  esac
+done
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+RED='\033[0;31m'
+GREEN='\033[0;32m'
+YELLOW='\033[1;33m'
+CYAN='\033[0;36m'
+BOLD='\033[1m'
+NC='\033[0m' # No Color
+
+PASS=0
+FAIL=0
+SKIP=0
+
+pass() {
+  PASS=$((PASS + 1))
+  echo -e "  ${GREEN}PASS${NC} $1"
+}
+
+fail() {
+  FAIL=$((FAIL + 1))
+  echo -e "  ${RED}FAIL${NC} $1"
+  if [ -n "${2:-}" ]; then
+    echo -e "       ${RED}$2${NC}"
+  fi
+}
+
+skip() {
+  SKIP=$((SKIP + 1))
+  echo -e "  ${YELLOW}SKIP${NC} $1"
+}
+
+info() {
+  echo -e "${CYAN}==>${NC} $1"
+}
+
+header() {
+  echo ""
+  echo -e "${BOLD}─── $1 ───${NC}"
+}
+
+# API helper: GET endpoint, return JSON body. Exits 1 on HTTP error.
+api_get() {
+  local path="$1"
+  curl -sf -H "${AUTH_HEADER}" "${API_URL}${path}" 2>/dev/null
+}
+
+# API helper: POST with optional JSON body
+api_post() {
+  local path="$1"
+  local body="${2:-}"
+  if [ -n "$body" ]; then
+    curl -sf -X POST -H "${AUTH_HEADER}" -H "Content-Type: application/json" \
+      -d "$body" "${API_URL}${path}" 2>/dev/null
+  else
+    curl -sf -X POST -H "${AUTH_HEADER}" "${API_URL}${path}" 2>/dev/null
+  fi
+}
+
+# Wait for an HTTP endpoint to return 200. Retries with backoff.
+wait_for_http() {
+  local url="$1"
+  local label="$2"
+  local max_wait="${3:-120}"
+  local elapsed=0
+  local interval=3
+
+  while [ $elapsed -lt $max_wait ]; do
+    if curl -sf -H "${AUTH_HEADER}" "$url" >/dev/null 2>&1; then
+      return 0
+    fi
+    sleep $interval
+    elapsed=$((elapsed + interval))
+  done
+  return 1
+}
+
+# Extract a field from JSON using python3 (no jq dependency)
+json_field() {
+  python3 -c "import sys,json; d=json.load(sys.stdin); print($1)" 2>/dev/null
+}
+
+# Wait for a job to reach a terminal state (Completed or Failed)
+# Usage: wait_for_job <cert_id> <max_seconds>
+# Returns 0 if Completed, 1 if Failed/timeout
+wait_for_jobs_done() {
+  local cert_id="$1"
+  local max_wait="${2:-180}"
+  local elapsed=0
+  local interval=5
+
+  while [ $elapsed -lt $max_wait ]; do
+    local jobs_json
+    jobs_json=$(api_get "/api/v1/jobs" 2>/dev/null || echo '{"data":[]}')
+
+    # Check if all jobs for this cert are in terminal state
+    # API returns jobs under "data" key (not "jobs")
+    local pending
+    pending=$(echo "$jobs_json" | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+jobs = data.get('data') or data.get('jobs') or []
+active = [j for j in jobs if j.get('certificate_id') == '$cert_id'
+          and j.get('status') not in ('Completed', 'Failed', 'Cancelled')]
+print(len(active))
+" 2>/dev/null || echo "99")
+
+    if [ "$pending" = "0" ]; then
+      # Check how many jobs exist and their terminal states
+      local job_counts
+      job_counts=$(echo "$jobs_json" | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+jobs = data.get('data') or data.get('jobs') or []
+mine = [j for j in jobs if j.get('certificate_id') == '$cert_id']
+completed = len([j for j in mine if j.get('status') == 'Completed'])
+failed = len([j for j in mine if j.get('status') in ('Failed', 'Cancelled')])
+print(f'{len(mine)} {completed} {failed}')
+" 2>/dev/null || echo "0 0 0")
+      local total_jobs completed_jobs failed_jobs
+      total_jobs=$(echo "$job_counts" | cut -d' ' -f1)
+      completed_jobs=$(echo "$job_counts" | cut -d' ' -f2)
+      failed_jobs=$(echo "$job_counts" | cut -d' ' -f3)
+
+      if [ "$completed_jobs" -gt 0 ]; then
+        return 0  # At least one job completed successfully
+      fi
+      if [ "$total_jobs" -gt 0 ] && [ "$failed_jobs" -gt 0 ]; then
+        return 1  # All jobs are in terminal state but none completed — all failed
+      fi
+    fi
+
+    sleep $interval
+    elapsed=$((elapsed + interval))
+  done
+  return 1
+}
+
+# Get the TLS cert subject from NGINX for a given SNI
+get_tls_subject() {
+  local sni="$1"
+  echo | openssl s_client -connect "$NGINX_TLS" -servername "$sni" 2>/dev/null \
+    | openssl x509 -noout -subject 2>/dev/null \
+    | sed 's/subject=//' | sed 's/^ *//'
+}
+
+get_tls_issuer() {
+  local sni="$1"
+  echo | openssl s_client -connect "$NGINX_TLS" -servername "$sni" 2>/dev/null \
+    | openssl x509 -noout -issuer 2>/dev/null \
+    | sed 's/issuer=//' | sed 's/^ *//'
+}
+
+# Get the TLS cert SANs from NGINX for a given SNI
+# Modern CAs (including Let's Encrypt / Pebble) put domains only in SAN, not Subject CN.
+get_tls_san() {
+  local sni="$1"
+  echo | openssl s_client -connect "$NGINX_TLS" -servername "$sni" 2>/dev/null \
+    | openssl x509 -noout -ext subjectAltName 2>/dev/null \
+    | grep -i "DNS:" | sed 's/^ *//'
+}
+
+# Check if NGINX is serving a cert that matches the given domain (checks Subject then SAN)
+check_tls_identity() {
+  local domain="$1"
+  local subject issuer san
+  subject=$(get_tls_subject "$domain")
+  issuer=$(get_tls_issuer "$domain")
+  san=$(get_tls_san "$domain")
+  if echo "$subject" | grep -qi "$domain" || echo "$san" | grep -qi "$domain"; then
+    echo "MATCH"
+    echo "Subject: $subject"
+    echo "SAN: $san"
+    echo "Issuer: $issuer"
+  else
+    echo "NO_MATCH"
+    echo "Subject: $subject"
+    echo "SAN: $san"
+    echo "Issuer: $issuer"
+  fi
+}
+
+# SQL exec in the postgres container
+psql_exec() {
+  docker exec certctl-test-postgres psql -U certctl -d certctl -tAc "$1" 2>/dev/null
+}
+
+# ---------------------------------------------------------------------------
+# Cleanup trap
+# ---------------------------------------------------------------------------
+cleanup() {
+  if [ "$TEARDOWN" = true ]; then
+    info "Tearing down test environment..."
+    docker compose -f "$COMPOSE_FILE" down -v >/dev/null 2>&1 || true
+  else
+    info "Leaving containers running (--no-teardown)"
+  fi
+}
+
+# ---------------------------------------------------------------------------
+# PHASE 0: Environment Check
+# ---------------------------------------------------------------------------
+header "Phase 0: Environment Check"
+
+# Make sure we're in the deploy directory
+if [ ! -f "$COMPOSE_FILE" ]; then
+  echo -e "${RED}ERROR: $COMPOSE_FILE not found.${NC}"
+  echo "Run this script from the certctl/deploy directory:"
+  echo "  cd certctl/deploy && ./test/run-test.sh"
+  exit 1
+fi
+
+for cmd in docker curl openssl python3; do
+  if command -v "$cmd" >/dev/null 2>&1; then
+    pass "$cmd available"
+  else
+    fail "$cmd not found" "Install $cmd and try again"
+    exit 1
+  fi
+done
+
+if docker compose version >/dev/null 2>&1; then
+  pass "docker compose available"
+else
+  fail "docker compose not available" "Install Docker Compose v2+"
+  exit 1
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 1: Start the Stack
+# ---------------------------------------------------------------------------
+header "Phase 1: Start Test Environment"
+
+# Teardown any previous run
+info "Cleaning up previous test environment..."
+docker compose -f "$COMPOSE_FILE" down -v >/dev/null 2>&1 || true
+
+# Set the cleanup trap AFTER the initial teardown
+trap cleanup EXIT
+
+if [ "$BUILD" = true ]; then
+  info "Building and starting containers (this takes 2-5 minutes on first run)..."
+  docker compose -f "$COMPOSE_FILE" up --build -d 2>&1 | tail -5
+else
+  info "Starting containers (--no-build)..."
+  docker compose -f "$COMPOSE_FILE" up -d 2>&1 | tail -5
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 2: Wait for Services
+# ---------------------------------------------------------------------------
+header "Phase 2: Waiting for Services"
+
+info "Waiting for PostgreSQL..."
+if docker compose -f "$COMPOSE_FILE" exec -T postgres pg_isready -U certctl -d certctl >/dev/null 2>&1 ||
+   wait_for_http "${API_URL}/health" "postgres" 60; then
+  pass "PostgreSQL ready"
+else
+  fail "PostgreSQL not ready after 60s"
+fi
+
+info "Waiting for certctl server..."
+if wait_for_http "${API_URL}/health" "server" 120; then
+  pass "certctl server healthy"
+  # Show trust setup + connector init for debugging
+  echo "  --- Server startup (trust setup) ---"
+  docker logs certctl-test-server 2>&1 | grep -E "trust|Added|Extract|provisioner|Pre-launch|key file|WARNING|CERTCTL_" | head -15
+  echo "  ---"
+else
+  fail "certctl server not healthy after 120s"
+  echo ""
+  echo "Server logs:"
+  docker logs certctl-test-server --tail 30
+  exit 1
+fi
+
+info "Waiting for NGINX..."
+if wait_for_http "http://localhost:8080" "nginx" 30; then
+  pass "NGINX healthy"
+else
+  # NGINX might not respond to plain curl on /health without the right path
+  # Check docker health instead
+  if docker inspect certctl-test-nginx --format='{{.State.Health.Status}}' 2>/dev/null | grep -q healthy; then
+    pass "NGINX healthy (docker healthcheck)"
+  else
+    skip "NGINX health check inconclusive (will verify via TLS later)"
+  fi
+fi
+
+# Give the agent a few seconds to register and send first heartbeat
+info "Waiting for agent heartbeat (up to 45s)..."
+AGENT_READY=false
+for i in $(seq 1 15); do
+  AGENT_STATUS=$(api_get "/api/v1/agents/agent-test-01" 2>/dev/null | python3 -c "import sys,json; print(json.load(sys.stdin).get('status',''))" 2>/dev/null || echo "")
+  if [ "$AGENT_STATUS" = "online" ]; then
+    AGENT_READY=true
+    break
+  fi
+  sleep 3
+done
+if [ "$AGENT_READY" = true ]; then
+  pass "Agent online"
+else
+  skip "Agent not yet online (may be slow to heartbeat — continuing)"
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 3: Verify Pre-Seeded Data
+# ---------------------------------------------------------------------------
+header "Phase 3: Verify Pre-Seeded Data"
+
+# Agents
+AGENT_COUNT=$(api_get "/api/v1/agents" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$AGENT_COUNT" -ge 2 ]; then
+  pass "Agents: $AGENT_COUNT found (agent-test-01 + server-scanner)"
+else
+  fail "Agents: expected >= 2, got $AGENT_COUNT"
+fi
+
+# Issuers
+ISSUER_COUNT=$(api_get "/api/v1/issuers" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$ISSUER_COUNT" -ge 3 ]; then
+  pass "Issuers: $ISSUER_COUNT found (iss-local, iss-acme-staging, iss-stepca)"
+else
+  fail "Issuers: expected >= 3, got $ISSUER_COUNT" "Check seed_test.sql loaded correctly"
+fi
+
+# Targets
+TARGET_COUNT=$(api_get "/api/v1/targets" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$TARGET_COUNT" -ge 1 ]; then
+  pass "Targets: $TARGET_COUNT found (target-test-nginx)"
+else
+  fail "Targets: expected >= 1, got $TARGET_COUNT" "seed_test.sql may have failed after iss-local"
+fi
+
+# Profile
+PROFILE_RESP=$(api_get "/api/v1/profiles" 2>/dev/null || echo '{"total":0}')
+PROFILE_COUNT=$(echo "$PROFILE_RESP" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$PROFILE_COUNT" -ge 2 ]; then
+  pass "Profiles: $PROFILE_COUNT found (prof-test-tls, prof-test-smime)"
+else
+  fail "Profiles: expected >= 1, got $PROFILE_COUNT"
+fi
+
+# Bail if seed data is broken
+if [ "$ISSUER_COUNT" -lt 3 ] || [ "$TARGET_COUNT" -lt 1 ]; then
+  echo ""
+  echo -e "${RED}Seed data is incomplete. Cannot continue.${NC}"
+  echo "Check PostgreSQL logs: docker logs certctl-test-postgres"
+  exit 1
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 4: Local CA Issuance
+# ---------------------------------------------------------------------------
+header "Phase 4: Local CA Certificate Issuance"
+
+info "Creating certificate record mc-local-test..."
+CREATE_RESP=$(api_post "/api/v1/certificates" '{
+  "id": "mc-local-test",
+  "name": "local-test-cert",
+  "common_name": "local.certctl.test",
+  "sans": ["local.certctl.test"],
+  "issuer_id": "iss-local",
+  "owner_id": "owner-test-admin",
+  "team_id": "team-test-ops",
+  "renewal_policy_id": "rp-default",
+  "certificate_profile_id": "prof-test-tls",
+  "environment": "development"
+}' 2>/dev/null || echo "ERROR")
+
+if echo "$CREATE_RESP" | python3 -c "import sys,json; d=json.load(sys.stdin); assert d.get('id')=='mc-local-test'" 2>/dev/null; then
+  pass "Certificate record created"
+else
+  fail "Certificate creation failed" "$CREATE_RESP"
+fi
+
+info "Linking certificate to NGINX target..."
+psql_exec "INSERT INTO certificate_target_mappings (certificate_id, target_id) VALUES ('mc-local-test', 'target-test-nginx') ON CONFLICT DO NOTHING;"
+pass "Target mapping inserted"
+
+info "Triggering issuance..."
+RENEW_RESP=$(api_post "/api/v1/certificates/mc-local-test/renew" 2>/dev/null || echo "ERROR")
+if echo "$RENEW_RESP" | grep -q "renewal_triggered\|status"; then
+  pass "Issuance triggered"
+else
+  fail "Trigger failed" "$RENEW_RESP"
+fi
+
+# Verify a job was created (this is the bug fix check)
+sleep 2
+JOB_COUNT=$(api_get "/api/v1/jobs" | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+jobs = [j for j in (data.get('data') or data.get('jobs') or []) if j.get('certificate_id') == 'mc-local-test']
+print(len(jobs))
+" 2>/dev/null || echo "0")
+
+if [ "$JOB_COUNT" -gt 0 ]; then
+  pass "Job created ($JOB_COUNT jobs for mc-local-test)"
+else
+  fail "No jobs created — TriggerRenewalWithActor bug still present"
+fi
+
+info "Waiting for issuance + deployment (up to 180s)..."
+if wait_for_jobs_done "mc-local-test" 180; then
+  pass "All jobs completed"
+else
+  fail "Jobs did not complete within 180s"
+  echo "  Current jobs:"
+  api_get "/api/v1/jobs" 2>/dev/null | python3 -m json.tool 2>/dev/null | head -30
+fi
+
+info "Reloading NGINX to pick up deployed certificate..."
+docker exec certctl-test-nginx nginx -s reload 2>/dev/null || true
+sleep 3
+
+info "Verifying TLS certificate on NGINX..."
+TLS_CHECK=$(check_tls_identity "local.certctl.test")
+TLS_RESULT=$(echo "$TLS_CHECK" | head -1)
+if [ "$TLS_RESULT" = "MATCH" ]; then
+  pass "NGINX serving cert for local.certctl.test"
+  echo "$TLS_CHECK" | tail -n +2 | while read -r line; do echo -e "       $line"; done
+else
+  fail "NGINX not serving expected cert" "$(echo "$TLS_CHECK" | tail -n +2 | tr '\n' ', ')"
+fi
+
+# Check cert status in API
+CERT_STATUS=$(api_get "/api/v1/certificates/mc-local-test" | python3 -c "import sys,json; print(json.load(sys.stdin).get('status',''))" 2>/dev/null || echo "unknown")
+if [ "$CERT_STATUS" = "Active" ]; then
+  pass "Certificate status: Active"
+else
+  skip "Certificate status: $CERT_STATUS (expected Active — may need more time)"
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 5: ACME (Pebble) Issuance
+# ---------------------------------------------------------------------------
+header "Phase 5: ACME (Pebble) Certificate Issuance"
+
+info "Creating certificate record mc-acme-test..."
+CREATE_RESP=$(api_post "/api/v1/certificates" '{
+  "id": "mc-acme-test",
+  "name": "acme-test-cert",
+  "common_name": "acme.certctl.test",
+  "sans": ["acme.certctl.test"],
+  "issuer_id": "iss-acme-staging",
+  "owner_id": "owner-test-admin",
+  "team_id": "team-test-ops",
+  "renewal_policy_id": "rp-default",
+  "certificate_profile_id": "prof-test-tls",
+  "environment": "staging"
+}' 2>/dev/null || echo "ERROR")
+
+if echo "$CREATE_RESP" | python3 -c "import sys,json; d=json.load(sys.stdin); assert d.get('id')=='mc-acme-test'" 2>/dev/null; then
+  pass "Certificate record created"
+else
+  fail "Certificate creation failed" "$CREATE_RESP"
+fi
+
+info "Linking to target and triggering issuance..."
+psql_exec "INSERT INTO certificate_target_mappings (certificate_id, target_id) VALUES ('mc-acme-test', 'target-test-nginx') ON CONFLICT DO NOTHING;"
+RENEW_RESP=$(api_post "/api/v1/certificates/mc-acme-test/renew" 2>/dev/null || echo "ERROR")
+if echo "$RENEW_RESP" | grep -q "renewal_triggered\|status"; then
+  pass "Issuance triggered"
+else
+  fail "Trigger failed" "$RENEW_RESP"
+fi
+
+info "Waiting for ACME issuance + deployment (up to 180s)..."
+if wait_for_jobs_done "mc-acme-test" 180; then
+  pass "All jobs completed"
+
+  info "Reloading NGINX to pick up deployed certificate..."
+  docker exec certctl-test-nginx nginx -s reload 2>/dev/null || true
+  sleep 3
+
+  TLS_CHECK=$(check_tls_identity "acme.certctl.test")
+  TLS_RESULT=$(echo "$TLS_CHECK" | head -1)
+  if [ "$TLS_RESULT" = "MATCH" ]; then
+    pass "NGINX serving cert for acme.certctl.test"
+    echo "$TLS_CHECK" | tail -n +2 | while read -r line; do echo -e "       $line"; done
+  else
+    fail "NGINX not serving expected ACME cert" "$(echo "$TLS_CHECK" | tail -n +2 | tr '\n' ', ')"
+  fi
+else
+  fail "ACME jobs did not complete within 180s"
+  info "Checking ACME job status..."
+  api_get "/api/v1/jobs" 2>/dev/null | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+for j in data.get('data', []):
+    if j.get('certificate_id') == 'mc-acme-test':
+        print(f\"  Job {j['id']}: type={j['type']} status={j['status']} error={j.get('last_error','')}\")" 2>/dev/null || true
+  echo "  Server logs (last 20 lines):"
+  docker logs certctl-test-server --tail 20 2>&1 | grep -i "acme\|error\|fail\|CSR" | head -10 || true
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 6: step-ca Issuance
+# ---------------------------------------------------------------------------
+header "Phase 6: step-ca (Private CA) Certificate Issuance"
+
+info "Creating certificate record mc-stepca-test..."
+CREATE_RESP=$(api_post "/api/v1/certificates" '{
+  "id": "mc-stepca-test",
+  "name": "stepca-test-cert",
+  "common_name": "stepca.certctl.test",
+  "sans": ["stepca.certctl.test"],
+  "issuer_id": "iss-stepca",
+  "owner_id": "owner-test-admin",
+  "team_id": "team-test-ops",
+  "renewal_policy_id": "rp-default",
+  "certificate_profile_id": "prof-test-tls",
+  "environment": "staging"
+}' 2>/dev/null || echo "ERROR")
+
+if echo "$CREATE_RESP" | python3 -c "import sys,json; d=json.load(sys.stdin); assert d.get('id')=='mc-stepca-test'" 2>/dev/null; then
+  pass "Certificate record created"
+else
+  fail "Certificate creation failed" "$CREATE_RESP"
+fi
+
+info "Linking to target and triggering issuance..."
+psql_exec "INSERT INTO certificate_target_mappings (certificate_id, target_id) VALUES ('mc-stepca-test', 'target-test-nginx') ON CONFLICT DO NOTHING;"
+RENEW_RESP=$(api_post "/api/v1/certificates/mc-stepca-test/renew" 2>/dev/null || echo "ERROR")
+if echo "$RENEW_RESP" | grep -q "renewal_triggered\|status"; then
+  pass "Issuance triggered"
+else
+  fail "Trigger failed" "$RENEW_RESP"
+fi
+
+info "Waiting for step-ca issuance + deployment (up to 120s)..."
+if wait_for_jobs_done "mc-stepca-test" 120; then
+  pass "All jobs completed"
+else
+  fail "Jobs did not complete in time"
+  info "Checking step-ca job status..."
+  api_get "/api/v1/jobs" 2>/dev/null | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+for j in data.get('data', []):
+    if j.get('certificate_id') == 'mc-stepca-test':
+        print(f\"  Job {j['id']}: type={j['type']} status={j['status']} error={j.get('last_error','')}\")" 2>/dev/null || true
+  echo "  Server logs (step-ca related):"
+  docker logs certctl-test-server --tail 30 2>&1 | grep -i "stepca\|step-ca\|provisioner\|jwe\|decrypt\|CSR.*fail\|error" | head -10 || true
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 7: Revocation
+# ---------------------------------------------------------------------------
+header "Phase 7: Revocation"
+
+info "Revoking mc-local-test (reason: superseded)..."
+REVOKE_RESP=$(api_post "/api/v1/certificates/mc-local-test/revoke" '{"reason": "superseded"}' 2>/dev/null || echo "ERROR")
+if echo "$REVOKE_RESP" | grep -qi "revoked\|status"; then
+  pass "Certificate revoked"
+else
+  fail "Revocation failed" "$REVOKE_RESP"
+fi
+
+info "Checking CRL..."
+CRL_RESP=$(api_get "/api/v1/crl" 2>/dev/null || echo '{"total":0}')
+CRL_TOTAL=$(echo "$CRL_RESP" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$CRL_TOTAL" -ge 1 ]; then
+  pass "CRL contains $CRL_TOTAL revoked certificate(s)"
+else
+  fail "CRL empty after revocation"
+fi
+
+CERT_STATUS=$(api_get "/api/v1/certificates/mc-local-test" | python3 -c "import sys,json; print(json.load(sys.stdin).get('status',''))" 2>/dev/null || echo "unknown")
+if [ "$CERT_STATUS" = "Revoked" ]; then
+  pass "Certificate status updated to Revoked"
+else
+  fail "Certificate status: $CERT_STATUS (expected Revoked)"
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 8: Discovery
+# ---------------------------------------------------------------------------
+header "Phase 8: Certificate Discovery"
+
+info "Checking discovered certificates..."
+DISC_RESP=$(api_get "/api/v1/discovered-certificates" 2>/dev/null || echo '{"total":0}')
+DISC_TOTAL=$(echo "$DISC_RESP" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$DISC_TOTAL" -ge 1 ]; then
+  pass "Discovered $DISC_TOTAL certificate(s) on filesystem"
+else
+  skip "No discovered certificates yet (agent scan may not have run)"
+fi
+
+SUMMARY_RESP=$(api_get "/api/v1/discovery-summary" 2>/dev/null || echo '{}')
+echo -e "       Discovery summary: $SUMMARY_RESP"
+
+# ---------------------------------------------------------------------------
+# PHASE 9: Renewal (re-issue ACME cert)
+# ---------------------------------------------------------------------------
+header "Phase 9: Renewal"
+
+# Try mc-stepca-test first (mc-local-test was revoked in Phase 7).
+# Fall back to mc-acme-test if step-ca cert isn't Active.
+RENEWAL_CERT=""
+for candidate in mc-stepca-test mc-acme-test; do
+  STATUS=$(api_get "/api/v1/certificates/$candidate" 2>/dev/null | python3 -c "import sys,json; print(json.load(sys.stdin).get('status',''))" 2>/dev/null || echo "unknown")
+  if [ "$STATUS" = "Active" ]; then
+    RENEWAL_CERT="$candidate"
+    break
+  fi
+done
+
+if [ -z "$RENEWAL_CERT" ]; then
+  skip "Cannot test renewal — no certificate in Active state"
+else
+  info "Using $RENEWAL_CERT for renewal test..."
+  info "Triggering renewal on $RENEWAL_CERT..."
+  RENEW_RESP=$(api_post "/api/v1/certificates/$RENEWAL_CERT/renew" 2>/dev/null || echo "ERROR")
+  if echo "$RENEW_RESP" | grep -q "renewal_triggered\|status"; then
+    pass "Renewal triggered"
+  else
+    skip "Renewal trigger returned: $RENEW_RESP"
+  fi
+
+  info "Waiting for renewal to complete (up to 180s)..."
+  if wait_for_jobs_done "$RENEWAL_CERT" 180; then
+    pass "Renewal jobs completed"
+
+    info "Reloading NGINX to pick up renewed certificate..."
+    docker exec certctl-test-nginx nginx -s reload 2>/dev/null || true
+    sleep 3
+
+    # Verify version history shows multiple versions
+    VERSIONS=$(api_get "/api/v1/certificates/$RENEWAL_CERT/versions" 2>/dev/null | python3 -c "import sys,json; d=json.load(sys.stdin); print(len(d) if isinstance(d, list) else d.get('total', 0))" 2>/dev/null || echo 0)
+    if [ "$VERSIONS" -ge 2 ]; then
+      pass "Certificate has $VERSIONS versions (original + renewal)"
+    else
+      skip "Expected 2+ versions, got $VERSIONS"
+    fi
+  else
+    skip "Renewal jobs did not complete within 180s"
+  fi
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 10: EST Enrollment (RFC 7030)
+# ---------------------------------------------------------------------------
+header "Phase 10: EST Enrollment (RFC 7030)"
+
+# Test cacerts endpoint — should return PKCS#7 with CA cert chain
+info "Testing EST cacerts endpoint..."
+EST_CACERTS_RESP=$(curl -sf -H "${AUTH_HEADER}" "${API_URL}/.well-known/est/cacerts" 2>/dev/null || echo "ERROR")
+if [ "$EST_CACERTS_RESP" != "ERROR" ] && [ -n "$EST_CACERTS_RESP" ]; then
+  # Response should be base64-encoded PKCS#7
+  if echo "$EST_CACERTS_RESP" | base64 -d >/dev/null 2>&1; then
+    pass "EST cacerts returns valid base64 PKCS#7 response"
+  else
+    fail "EST cacerts returned non-base64 data"
+  fi
+else
+  fail "EST cacerts endpoint failed" "$EST_CACERTS_RESP"
+fi
+
+# Test csrattrs endpoint
+info "Testing EST csrattrs endpoint..."
+EST_CSRATTRS_STATUS=$(curl -sf -o /dev/null -w "%{http_code}" -H "${AUTH_HEADER}" "${API_URL}/.well-known/est/csrattrs" 2>/dev/null || echo "000")
+if [ "$EST_CSRATTRS_STATUS" = "200" ] || [ "$EST_CSRATTRS_STATUS" = "204" ]; then
+  pass "EST csrattrs returns $EST_CSRATTRS_STATUS"
+else
+  fail "EST csrattrs returned $EST_CSRATTRS_STATUS (expected 200 or 204)"
+fi
+
+# Test simpleenroll — generate CSR, POST as base64-encoded DER
+info "Testing EST simpleenroll with generated CSR..."
+EST_KEY_FILE=$(mktemp /tmp/est-key-XXXXXX.pem)
+EST_CSR_PEM_FILE=$(mktemp /tmp/est-csr-XXXXXX.pem)
+EST_CSR_DER_FILE=$(mktemp /tmp/est-csr-XXXXXX.der)
+trap "rm -f $EST_KEY_FILE $EST_CSR_PEM_FILE $EST_CSR_DER_FILE" EXIT
+
+# Generate ECDSA key + CSR
+openssl ecparam -genkey -name prime256v1 -noout -out "$EST_KEY_FILE" 2>/dev/null
+openssl req -new -key "$EST_KEY_FILE" -out "$EST_CSR_PEM_FILE" -subj "/CN=est-device.certctl.test" 2>/dev/null
+openssl req -in "$EST_CSR_PEM_FILE" -out "$EST_CSR_DER_FILE" -outform DER 2>/dev/null
+
+# base64-encode the DER CSR (EST wire format)
+EST_CSR_B64=$(base64 < "$EST_CSR_DER_FILE" | tr -d '\n')
+
+EST_ENROLL_RESP=$(curl -sf \
+  -X POST \
+  -H "${AUTH_HEADER}" \
+  -H "Content-Type: application/pkcs10" \
+  -d "$EST_CSR_B64" \
+  "${API_URL}/.well-known/est/simpleenroll" 2>/dev/null || echo "ERROR")
+
+if [ "$EST_ENROLL_RESP" != "ERROR" ] && [ -n "$EST_ENROLL_RESP" ]; then
+  # Response should be base64-encoded PKCS#7 containing the issued cert
+  if echo "$EST_ENROLL_RESP" | base64 -d >/dev/null 2>&1; then
+    pass "EST simpleenroll issued certificate via PKCS#7 response"
+  else
+    fail "EST simpleenroll returned non-base64 data"
+  fi
+else
+  fail "EST simpleenroll failed" "$(curl -s -X POST -H "${AUTH_HEADER}" -H "Content-Type: application/pkcs10" -d "$EST_CSR_B64" "${API_URL}/.well-known/est/simpleenroll" 2>&1 | head -5)"
+fi
+
+# Test simplereenroll (should work identically)
+info "Testing EST simplereenroll..."
+EST_REENROLL_STATUS=$(curl -sf -o /dev/null -w "%{http_code}" \
+  -X POST \
+  -H "${AUTH_HEADER}" \
+  -H "Content-Type: application/pkcs10" \
+  -d "$EST_CSR_B64" \
+  "${API_URL}/.well-known/est/simplereenroll" 2>/dev/null || echo "000")
+
+if [ "$EST_REENROLL_STATUS" = "200" ]; then
+  pass "EST simplereenroll works (status 200)"
+else
+  fail "EST simplereenroll returned $EST_REENROLL_STATUS (expected 200)"
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 11: S/MIME Certificate Issuance
+# ---------------------------------------------------------------------------
+header "Phase 11: S/MIME Certificate Issuance"
+
+info "Creating S/MIME certificate record..."
+SMIME_RESP=$(api_post "/api/v1/certificates" '{
+  "id": "mc-smime-test",
+  "name": "smime-test-cert",
+  "common_name": "testuser@certctl.test",
+  "sans": ["testuser@certctl.test"],
+  "issuer_id": "iss-local",
+  "owner_id": "owner-test-admin",
+  "team_id": "team-test-ops",
+  "renewal_policy_id": "rp-default",
+  "certificate_profile_id": "prof-test-smime",
+  "environment": "staging"
+}' 2>/dev/null || echo "ERROR")
+
+if echo "$SMIME_RESP" | python3 -c "import sys,json; d=json.load(sys.stdin); assert d.get('id')=='mc-smime-test'" 2>/dev/null; then
+  pass "S/MIME certificate record created"
+else
+  fail "S/MIME certificate creation failed" "$SMIME_RESP"
+fi
+
+info "Linking S/MIME cert to target (needed for agent work routing)..."
+psql_exec "INSERT INTO certificate_target_mappings (certificate_id, target_id) VALUES ('mc-smime-test', 'target-test-nginx') ON CONFLICT DO NOTHING;"
+
+info "Triggering S/MIME issuance..."
+SMIME_RENEW=$(api_post "/api/v1/certificates/mc-smime-test/renew" 2>/dev/null || echo "ERROR")
+if echo "$SMIME_RENEW" | grep -q "renewal_triggered\|status"; then
+  pass "S/MIME issuance triggered"
+else
+  fail "S/MIME trigger failed" "$SMIME_RENEW"
+fi
+
+info "Waiting for S/MIME issuance (up to 120s)..."
+if wait_for_jobs_done "mc-smime-test" 120; then
+  pass "S/MIME jobs completed"
+
+  # Fetch the issued cert and verify EKU
+  info "Verifying S/MIME certificate EKU..."
+  SMIME_VERSIONS=$(api_get "/api/v1/certificates/mc-smime-test/versions" 2>/dev/null || echo "[]")
+  SMIME_PEM=$(echo "$SMIME_VERSIONS" | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+versions = data if isinstance(data, list) else data.get('data', [])
+if versions:
+    print(versions[-1].get('pem_chain', versions[-1].get('pem', '')))
+" 2>/dev/null || echo "")
+
+  if [ -n "$SMIME_PEM" ]; then
+    # Parse the cert and check for emailProtection EKU
+    SMIME_EKU=$(echo "$SMIME_PEM" | openssl x509 -noout -text 2>/dev/null | grep -A2 "Extended Key Usage" || echo "")
+    if echo "$SMIME_EKU" | grep -qi "emailProtection\|E-mail Protection"; then
+      pass "S/MIME cert has emailProtection EKU"
+    else
+      fail "S/MIME cert missing emailProtection EKU" "Got: $SMIME_EKU"
+    fi
+
+    # Check KeyUsage flags (S/MIME should have Digital Signature + Content Commitment)
+    SMIME_KU=$(echo "$SMIME_PEM" | openssl x509 -noout -text 2>/dev/null | awk '/X509v3 Key Usage:/{getline; print; exit}')
+    if echo "$SMIME_KU" | grep -qi "Digital Signature"; then
+      pass "S/MIME cert has Digital Signature KeyUsage"
+    else
+      fail "S/MIME cert missing Digital Signature KeyUsage" "Got: $SMIME_KU"
+    fi
+
+    # Check that email SAN is present
+    SMIME_SAN=$(echo "$SMIME_PEM" | openssl x509 -noout -ext subjectAltName 2>/dev/null || echo "")
+    if echo "$SMIME_SAN" | grep -qi "email:testuser@certctl.test"; then
+      pass "S/MIME cert has email SAN"
+    else
+      # Some implementations use rfc822Name instead of email:
+      if echo "$SMIME_SAN" | grep -qi "testuser@certctl.test"; then
+        pass "S/MIME cert has email SAN (rfc822Name)"
+      else
+        skip "S/MIME email SAN not found in cert (may be in CN only)"
+        echo "       SAN content: $SMIME_SAN"
+      fi
+    fi
+  else
+    skip "Could not extract S/MIME cert PEM for EKU verification"
+  fi
+else
+  fail "S/MIME issuance did not complete within 120s"
+  info "Checking S/MIME job status..."
+  api_get "/api/v1/jobs" 2>/dev/null | python3 -c "
+import sys, json
+data = json.load(sys.stdin)
+for j in data.get('data', []):
+    if j.get('certificate_id') == 'mc-smime-test':
+        print(f\"  Job {j['id']}: type={j['type']} status={j['status']} error={j.get('last_error','')}\")" 2>/dev/null || true
+fi
+
+# ---------------------------------------------------------------------------
+# PHASE 12: API Spot Checks
+# ---------------------------------------------------------------------------
+header "Phase 12: API Spot Checks"
+
+# Health
+if api_get "/health" >/dev/null 2>&1; then
+  pass "GET /health returns 200"
+else
+  fail "GET /health failed"
+fi
+
+# Metrics
+METRICS_RESP=$(api_get "/api/v1/metrics" 2>/dev/null || echo "ERROR")
+if echo "$METRICS_RESP" | python3 -c "import sys,json; d=json.load(sys.stdin); assert 'gauge' in d" 2>/dev/null; then
+  pass "GET /api/v1/metrics returns valid JSON"
+else
+  fail "Metrics endpoint broken"
+fi
+
+# Stats summary
+STATS_RESP=$(api_get "/api/v1/stats/summary" 2>/dev/null || echo "ERROR")
+if echo "$STATS_RESP" | python3 -c "import sys,json; json.load(sys.stdin)" 2>/dev/null; then
+  pass "GET /api/v1/stats/summary returns valid JSON"
+else
+  fail "Stats summary endpoint broken"
+fi
+
+# Audit trail
+AUDIT_RESP=$(api_get "/api/v1/audit" 2>/dev/null || echo '{"total":0}')
+AUDIT_TOTAL=$(echo "$AUDIT_RESP" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+if [ "$AUDIT_TOTAL" -gt 0 ]; then
+  pass "Audit trail: $AUDIT_TOTAL events recorded"
+else
+  fail "Audit trail empty"
+fi
+
+# Jobs summary
+JOBS_RESP=$(api_get "/api/v1/jobs" 2>/dev/null || echo '{"total":0}')
+JOBS_TOTAL=$(echo "$JOBS_RESP" | python3 -c "import sys,json; print(json.load(sys.stdin).get('total',0))" 2>/dev/null || echo 0)
+pass "Total jobs created: $JOBS_TOTAL"
+
+# Prometheus
+PROM_RESP=$(curl -sf -H "${AUTH_HEADER}" "${API_URL}/api/v1/metrics/prometheus" 2>/dev/null || echo "")
+if echo "$PROM_RESP" | grep -q "certctl_certificate_total"; then
+  pass "Prometheus metrics endpoint working"
+else
+  fail "Prometheus metrics endpoint broken"
+fi
+
+# ---------------------------------------------------------------------------
+# Summary
+# ---------------------------------------------------------------------------
+header "Test Summary"
+
+TOTAL=$((PASS + FAIL + SKIP))
+echo ""
+echo -e "  ${GREEN}Passed: $PASS${NC}"
+echo -e "  ${RED}Failed: $FAIL${NC}"
+echo -e "  ${YELLOW}Skipped: $SKIP${NC}"
+echo -e "  Total:  $TOTAL"
+echo ""
+
+if [ "$FAIL" -eq 0 ]; then
+  echo -e "${GREEN}${BOLD}All tests passed.${NC}"
+  exit 0
+else
+  echo -e "${RED}${BOLD}$FAIL test(s) failed.${NC}"
+  echo ""
+  echo "Useful debug commands:"
+  echo "  docker logs certctl-test-server --tail 50"
+  echo "  docker logs certctl-test-agent --tail 50"
+  echo "  docker compose -f $COMPOSE_FILE ps"
+  exit 1
+fi

deploy/test/setup-trust.sh

@@ -0,0 +1,140 @@
+#!/bin/sh
+# This script runs inside the certctl-server container at startup.
+# It fetches CA certificates from Pebble and step-ca, adds them to the
+# system trust store, then starts the certctl server.
+#
+# Why: The ACME connector and step-ca connector use Go's default http.Client
+# with no InsecureSkipVerify. They rely on the system trust store to verify
+# TLS connections. Pebble and step-ca both use self-signed root CAs that
+# aren't in Alpine's default CA bundle, so we must add them manually.
+#
+# This script runs as root (user: "0:0" in docker-compose) so that
+# update-ca-certificates can write to /etc/ssl/certs/.
+
+set -e
+
+echo "=== certctl trust store setup ==="
+
+# --- Pebble CA cert (fetched from management API) ---
+# Pebble's management API serves the root CA at /roots/0.
+# We use -k because we can't verify Pebble's TLS cert yet (chicken-and-egg).
+echo "Fetching Pebble root CA from management API..."
+PEBBLE_CA=""
+for i in 1 2 3 4 5 6 7 8 9 10; do
+    if PEBBLE_CA=$(curl -sk https://pebble:15000/roots/0 2>/dev/null); then
+        if [ -n "$PEBBLE_CA" ]; then
+            echo "$PEBBLE_CA" > /usr/local/share/ca-certificates/pebble-ca.crt
+            echo "  Added: Pebble test CA"
+            break
+        fi
+    fi
+    echo "  Waiting for Pebble (attempt $i/10)..."
+    sleep 2
+done
+
+if [ -z "$PEBBLE_CA" ]; then
+    echo "  WARNING: Could not fetch Pebble CA. ACME issuance will fail."
+fi
+
+# --- step-ca root cert (from shared volume) ---
+# The step-ca container writes its root CA to /home/step/certs/root_ca.crt.
+# We mount the step-ca data volume at /stepca-data inside this container.
+STEPCA_ROOT="/stepca-data/certs/root_ca.crt"
+echo "Waiting for step-ca root cert..."
+for i in 1 2 3 4 5 6 7 8 9 10; do
+    if [ -f "$STEPCA_ROOT" ]; then
+        cp "$STEPCA_ROOT" /usr/local/share/ca-certificates/step-ca-root.crt
+        echo "  Added: step-ca root CA"
+        break
+    fi
+    echo "  Waiting for step-ca root cert (attempt $i/10)..."
+    sleep 2
+done
+
+if [ ! -f "$STEPCA_ROOT" ]; then
+    echo "  WARNING: step-ca root cert not found at $STEPCA_ROOT"
+    echo "  step-ca issuance may fail until the cert is available."
+fi
+
+# --- step-ca provisioner key (extracted from ca.json) ---
+# When step-ca auto-bootstraps via DOCKER_STEPCA_INIT_* env vars, the
+# encrypted provisioner key (JWE) is NOT written as a separate file.
+# Instead, it's embedded in ca.json under:
+#   authority.provisioners[0].encryptedKey
+# We extract it here and write to /tmp so the certctl server can read it.
+# The stepca_data volume is mounted :ro, so we can't write there.
+STEPCA_CA_JSON="/stepca-data/config/ca.json"
+STEPCA_KEY_EXTRACTED="/tmp/step-ca-provisioner-key"
+echo "Extracting step-ca provisioner key from ca.json..."
+for i in 1 2 3 4 5 6 7 8 9 10; do
+    if [ -f "$STEPCA_CA_JSON" ]; then
+        # Extract the encryptedKey value using grep+sed (no jq in Alpine base)
+        # The field looks like: "encryptedKey": "eyJhbGciOi..."
+        ENCRYPTED_KEY=$(grep -o '"encryptedKey":"[^"]*"' "$STEPCA_CA_JSON" | head -1 | sed 's/"encryptedKey":"//;s/"$//')
+        if [ -z "$ENCRYPTED_KEY" ]; then
+            # Try with spaces around colon (JSON formatting varies)
+            ENCRYPTED_KEY=$(grep -o '"encryptedKey" *: *"[^"]*"' "$STEPCA_CA_JSON" | head -1 | sed 's/"encryptedKey" *: *"//;s/"$//')
+        fi
+        if [ -n "$ENCRYPTED_KEY" ]; then
+            # Check if it's JWE compact serialization (dot-separated) or JSON serialization
+            case "$ENCRYPTED_KEY" in
+                \{*)
+                    # Already JSON serialization — write as-is
+                    echo "$ENCRYPTED_KEY" > "$STEPCA_KEY_EXTRACTED"
+                    ;;
+                *)
+                    # JWE compact serialization: header.encrypted_key.iv.ciphertext.tag
+                    # Convert to JSON serialization expected by Go decryptProvisionerKey()
+                    JWE_PROTECTED=$(echo "$ENCRYPTED_KEY" | cut -d. -f1)
+                    JWE_ENCKEY=$(echo "$ENCRYPTED_KEY" | cut -d. -f2)
+                    JWE_IV=$(echo "$ENCRYPTED_KEY" | cut -d. -f3)
+                    JWE_CT=$(echo "$ENCRYPTED_KEY" | cut -d. -f4)
+                    JWE_TAG=$(echo "$ENCRYPTED_KEY" | cut -d. -f5)
+                    printf '{"protected":"%s","encrypted_key":"%s","iv":"%s","ciphertext":"%s","tag":"%s"}' \
+                        "$JWE_PROTECTED" "$JWE_ENCKEY" "$JWE_IV" "$JWE_CT" "$JWE_TAG" > "$STEPCA_KEY_EXTRACTED"
+                    ;;
+            esac
+            echo "  Extracted provisioner key to $STEPCA_KEY_EXTRACTED"
+            echo "  Key file size: $(wc -c < "$STEPCA_KEY_EXTRACTED") bytes"
+            echo "  Key starts with: $(head -c 40 "$STEPCA_KEY_EXTRACTED")..."
+            # Override the env var so the server reads from the extracted file
+            export CERTCTL_STEPCA_KEY_PATH="$STEPCA_KEY_EXTRACTED"
+            break
+        else
+            echo "  ca.json found but encryptedKey not found in it (attempt $i/10)"
+        fi
+    else
+        echo "  Waiting for step-ca ca.json (attempt $i/10)..."
+    fi
+    sleep 2
+done
+
+if [ ! -f "$STEPCA_KEY_EXTRACTED" ]; then
+    echo "  WARNING: Could not extract step-ca provisioner key"
+    echo "  Listing /stepca-data/config/ for debugging:"
+    ls -la /stepca-data/config/ 2>/dev/null || echo "  /stepca-data/config/ does not exist"
+    echo "  step-ca issuance will fail."
+fi
+
+# --- Update system trust store ---
+echo "Updating system CA trust store..."
+update-ca-certificates 2>/dev/null || true
+
+echo "Trust store updated."
+
+# --- Debug: verify configuration before starting server ---
+echo "=== Pre-launch verification ==="
+echo "  CERTCTL_STEPCA_KEY_PATH=$CERTCTL_STEPCA_KEY_PATH"
+if [ -f "$CERTCTL_STEPCA_KEY_PATH" ]; then
+    echo "  step-ca key file exists ($(wc -c < "$CERTCTL_STEPCA_KEY_PATH") bytes)"
+    echo "  step-ca key preview: $(head -c 60 "$CERTCTL_STEPCA_KEY_PATH")..."
+else
+    echo "  WARNING: step-ca key file NOT FOUND at $CERTCTL_STEPCA_KEY_PATH"
+fi
+echo "  CERTCTL_ACME_DIRECTORY_URL=$CERTCTL_ACME_DIRECTORY_URL"
+echo "  CERTCTL_ACME_INSECURE=$CERTCTL_ACME_INSECURE"
+echo "  Pebble CA cert: $(ls -la /usr/local/share/ca-certificates/pebble-ca.crt 2>/dev/null || echo 'NOT FOUND')"
+echo "  step-ca root cert: $(ls -la /usr/local/share/ca-certificates/step-ca-root.crt 2>/dev/null || echo 'NOT FOUND')"
+echo "  System CA count: $(ls /etc/ssl/certs/*.pem 2>/dev/null | wc -l) PEM files"
+echo "=== Starting certctl server ==="
+exec /app/server

docs/architecture.md

@@ -80,13 +80,16 @@ flowchart TB
         CA2["ACME\n(HTTP-01 + DNS-01 + DNS-PERSIST-01)\n(EAB, ZeroSSL auto-EAB)"]
         CA3["step-ca\n(/sign API)"]
         CA4["OpenSSL / Custom CA\n(script-based)"]
-        CA6["Vault PKI\n(planned)"]
+        CA6["Vault PKI\n(token auth, /sign API)"]
+        CA7["DigiCert CertCentral\n(async order model)"]
     end
 
     subgraph "Target Systems"
         T1["NGINX\n(file write + reload)"]
         T4["Apache httpd\n(file write + reload)"]
         T5["HAProxy\n(combined PEM + reload)"]
+        T6["Traefik\n(file provider)"]
+        T7["Caddy\n(admin API / file)"]
         T2["F5 BIG-IP\n(proxy agent + iControl REST, planned)"]
         T3["IIS\n(agent-local PowerShell, planned)"]
     end
@@ -96,7 +99,7 @@ flowchart TB
     SVC --> REPO
     REPO --> PG
     SCHED --> SVC
-    SVC -->|"Issue/Renew"| CA1 & CA2 & CA3
+    SVC -->|"Issue/Renew"| CA1 & CA2 & CA3 & CA4 & CA6 & CA7
 
     A1 & A2 & A3 -->|"CSR + Heartbeat"| API
     API -->|"Cert + Chain\n(NO private key)"| A1 & A2 & A3
@@ -414,7 +417,7 @@ The agent deploys certificates using target connectors. Each connector knows how
 - **Apache httpd**: Writes separate cert/chain/key files, validates with `apachectl configtest`, graceful reload
 - **HAProxy**: Builds a combined PEM file (cert + chain + key), optionally validates config, reloads via systemctl or signal
 - **F5 BIG-IP** (planned): A proxy agent in the same network zone calls the iControl REST API to upload certificate and update SSL profile bindings. The server assigns the work; the proxy agent executes it.
-- **IIS** (planned, dual-mode): (1) Agent-local (recommended) — a Windows agent on the IIS box runs PowerShell `Import-PfxCertificate` + `Set-WebBinding` directly. (2) Proxy agent WinRM — for agentless IIS targets, a nearby Windows agent reaches the IIS box via WinRM.
+- **IIS** (implemented, dual-mode): (1) Agent-local (recommended) — a Windows agent on the IIS box runs PowerShell `Import-PfxCertificate` + `Set-WebBinding` directly with PFX conversion and SHA-1 thumbprint computation. (2) Proxy agent WinRM — for agentless IIS targets, a nearby Windows agent reaches the IIS box via WinRM.
 
 The agent handles both the certificate (public) and the private key (read from local key store at `CERTCTL_KEY_DIR`). The control plane never sees the private key and never initiates outbound connections to agents or targets (pull-only model).
 
@@ -506,7 +509,8 @@ flowchart TB
         II --> ACME["ACME v2"]
         II --> SC["step-ca"]
         II --> OC["OpenSSL / Custom CA"]
-        II --> VP["Vault PKI (planned)"]
+        II --> VP["Vault PKI"]
+        II --> DC["DigiCert CertCentral"]
     end
 
     subgraph "Target Connectors"

docs/connectors.md

@@ -21,9 +21,10 @@ Connectors extend certctl to integrate with external systems for certificate iss
    - [Built-in: Apache httpd](#built-in-apache-httpd)
    - [Built-in: HAProxy](#built-in-haproxy)
    - [Built-in: Traefik](#built-in-traefik)
+   - [Built-in: Envoy](#built-in-envoy)
    - [Built-in: Caddy](#built-in-caddy)
    - [F5 BIG-IP (Interface Only)](#f5-big-ip-interface-only)
-   - [IIS (Interface Only, Dual-Mode)](#iis-interface-only-dual-mode)
+   - [IIS (Implemented, Dual-Mode)](#iis-implemented-dual-mode)
 4. [Notifier Connector](#notifier-connector)
    - [Interface](#interface-2)
 5. [Registering a Connector](#registering-a-connector)
@@ -52,7 +53,7 @@ Connectors extend certctl to integrate with external systems for certificate iss
 Three types of connectors:
 
 1. **Issuer Connector** — Obtains certificates from CAs (Local CA with sub-CA support, ACME with HTTP-01 + DNS-01 + DNS-PERSIST-01, step-ca, OpenSSL/Custom CA implemented; additional CA integrations planned)
-2. **Target Connector** — Deploys certificates to infrastructure (NGINX, Apache httpd, HAProxy, Traefik, Caddy implemented; F5 via proxy agent, IIS dual-mode interface only; additional cloud and network targets planned)
+2. **Target Connector** — Deploys certificates to infrastructure (NGINX, Apache httpd, HAProxy, Traefik, Caddy, Envoy, IIS implemented; F5 via proxy agent planned; additional cloud and network targets planned)
 3. **Notifier Connector** — Sends alerts about certificate events (Email, Webhooks, Slack, Microsoft Teams, PagerDuty, OpsGenie implemented)
 
 All connectors accept JSON configuration at initialization, support config validation, and are registered in the service layer. Issuer connectors run on the control plane; target connectors run on agents. For network appliances where agents can't be installed, a **proxy agent** in the same network zone handles deployment — the server never initiates outbound connections.
@@ -590,6 +591,35 @@ When `mode` is `"api"`, the connector posts the certificate to the admin API end
 
 Location: `internal/connector/target/caddy/caddy.go`
 
+### Built-in: Envoy
+
+The Envoy connector uses file-based certificate delivery — it writes certificate and key files to a directory that Envoy watches via its SDS (Secret Discovery Service) file-based configuration or static `filename` references in the bootstrap config. When files change, Envoy automatically picks up the new certificates without requiring a reload command.
+
+Configuration:
+```json
+{
+  "cert_dir": "/etc/envoy/certs",
+  "cert_filename": "cert.pem",
+  "key_filename": "key.pem",
+  "chain_filename": "chain.pem",
+  "sds_config": true
+}
+```
+
+| Field | Type | Default | Description |
+|-------|------|---------|-------------|
+| `cert_dir` | string | (required) | Directory where Envoy watches for certificate files |
+| `cert_filename` | string | `cert.pem` | Filename for the certificate (leaf + chain unless `chain_filename` is set) |
+| `key_filename` | string | `key.pem` | Filename for the private key |
+| `chain_filename` | string | (empty) | If set, chain is written to a separate file instead of appended to the cert |
+| `sds_config` | bool | `false` | If true, writes an `sds.json` file for Envoy's file-based SDS provider |
+
+When `sds_config` is `true`, the connector writes an SDS JSON file (`{cert_dir}/sds.json`) containing a `tls_certificate` resource that points to the cert and key file paths. Envoy's file-based SDS (`path_config_source`) watches this file for changes, providing automatic hot-reload of certificates. This is the recommended approach for production Envoy deployments using dynamic TLS configuration.
+
+When `sds_config` is `false` (the default), the connector simply writes cert and key files. Use this mode when Envoy's bootstrap config references the cert/key files directly via static `filename` fields in the TLS context.
+
+Location: `internal/connector/target/envoy/envoy.go`
+
 ### F5 BIG-IP (Interface Only)
 
 The F5 BIG-IP target connector interface is defined with the iControl REST flow mapped out, but the actual API calls are not yet implemented. F5 appliances can't run agents directly, so this connector uses the **proxy agent pattern**: a designated agent in the same network zone picks up F5 deployment jobs and calls the iControl REST API. The server assigns the work; the proxy agent executes it.
@@ -611,30 +641,76 @@ Note: F5 credentials are stored on the proxy agent, not on the control plane ser
 
 Location: `internal/connector/target/f5/f5.go`
 
-### IIS (Interface Only, Dual-Mode)
+### IIS (Implemented, Dual-Mode)
 
-The IIS target connector supports two planned deployment modes:
+The IIS target connector supports two deployment modes — agent-local (recommended) and proxy agent WinRM for agentless targets.
 
-**Agent-local (recommended):** A Windows agent runs directly on the IIS server and deploys certificates using PowerShell — `Import-PfxCertificate` to install into the certificate store and `Set-WebBinding` to bind to the IIS site. This is the preferred approach: no remote access needed, no credential management, same pull-based model as NGINX/Apache/HAProxy.
+**Agent-local (recommended):** A Windows agent runs directly on the IIS server and deploys certificates using PowerShell — `Import-PfxCertificate` to install into the certificate store and `Set-WebBinding` to bind to the IIS site. The agent handles PEM-to-PFX conversion via `go-pkcs12`, computes SHA-1 thumbprint from the certificate, and executes parameterized PowerShell scripts for injection-safe binding management. This is the preferred approach: no remote access needed, no credential management, same pull-based model as NGINX/Apache/HAProxy.
 
-**Proxy agent WinRM (for agentless targets):** For Windows servers where you don't want to install an agent, a nearby Windows agent acts as a proxy and reaches the IIS box via WinRM. The proxy agent picks up the deployment job, transfers the PFX bundle over WinRM, and runs the PowerShell commands remotely. WinRM credentials are stored on the proxy agent, not on the control plane.
+**Proxy agent WinRM (for agentless targets):** For Windows servers where you don't want to install an agent, a Linux or Windows proxy agent in the same network zone connects via WinRM (Windows Remote Management) and executes PowerShell commands remotely. The PFX bundle is base64-encoded, transferred inline in the WinRM session, decoded to a temp file on the remote host, imported, and the temp file is cleaned up in a `try/finally` block. WinRM credentials are configured on the target, not on the control plane. Uses the `masterzen/winrm` Go library with support for Basic, NTLM, and Kerberos authentication.
 
-Configuration (defined, not yet functional):
+**Agent-local configuration:**
 ```json
 {
-  "mode": "local",
+  "hostname": "iis-server.example.com",
   "site_name": "Default Web Site",
   "cert_store": "WebHosting",
-  "winrm_host": "",
-  "winrm_username": "",
-  "winrm_password": "",
-  "winrm_use_https": true
+  "port": 443,
+  "sni": true,
+  "ip_address": "*",
+  "binding_info": "www.example.com"
 }
 ```
 
-When `mode` is `"local"`, the `winrm_*` fields are ignored. When `mode` is `"proxy"`, the agent connects to the remote IIS server via WinRM using the provided credentials.
+**WinRM proxy configuration:**
+```json
+{
+  "hostname": "iis-server.example.com",
+  "site_name": "Default Web Site",
+  "cert_store": "WebHosting",
+  "port": 443,
+  "sni": true,
+  "ip_address": "*",
+  "mode": "winrm",
+  "winrm": {
+    "winrm_host": "iis-server.example.com",
+    "winrm_port": 5985,
+    "winrm_username": "Administrator",
+    "winrm_password": "...",
+    "winrm_https": false,
+    "winrm_insecure": false,
+    "winrm_timeout": 60
+  }
+}
+```
 
-Location: `internal/connector/target/iis/iis.go`
+**Configuration Fields:**
+- `hostname` (string, required): IIS server hostname or FQDN
+- `site_name` (string, required): IIS website name (e.g., "Default Web Site")
+- `cert_store` (string, required): Certificate store for import (e.g., "WebHosting", "My")
+- `port` (number, default 443): HTTPS binding port
+- `sni` (boolean, default false): Enable Server Name Indication (SNI)
+- `ip_address` (string, default "*"): Specific IP to bind to, or "*" for all IPs
+- `binding_info` (string, optional): Host header for SNI bindings
+- `mode` (string, default "local"): Deployment mode — `local` (agent-local PowerShell) or `winrm` (remote via WinRM)
+
+**WinRM fields (required when `mode` is `winrm`):**
+- `winrm.winrm_host` (string, required): Remote Windows server hostname or IP
+- `winrm.winrm_port` (number, default 5985 HTTP / 5986 HTTPS): WinRM listener port
+- `winrm.winrm_username` (string, required): Windows account with admin privileges
+- `winrm.winrm_password` (string, required): Account password
+- `winrm.winrm_https` (boolean, default false): Use HTTPS transport
+- `winrm.winrm_insecure` (boolean, default false): Skip TLS certificate verification
+- `winrm.winrm_timeout` (number, default 60): Operation timeout in seconds
+
+**Security Model:**
+- PFX files are transient — generated with random passwords, deleted after import
+- In WinRM mode, PFX data is base64-encoded and transferred inline (no SMB/file share needed), with remote temp file cleanup in `try/finally`
+- PowerShell commands use parameterized values — IIS names and cert stores are regex-validated before script execution
+- Field names are validated against `^[a-zA-Z0-9 _\-\.]+$` to prevent PowerShell injection
+- Certificate thumbprints computed via SHA-1 for IIS binding lookups
+
+Location: `internal/connector/target/iis/iis.go`, `internal/connector/target/iis/winrm.go`
 
 ## Notifier Connector
 

docs/features.md

@@ -1469,8 +1469,8 @@ Each guide includes an evidence summary table mapping specific criteria to certc
 | **Bulk revocation** | ✗ | ✓ | Planned V3 (paid) |
 | **Certificate health scores** | ✗ | ✓ | Planned V3 |
 | **Compliance scoring** | ✗ | ✓ | Planned V3 |
-| **DigiCert issuer** | ✗ | ✓ | Planned V2.1 (free) |
-| **Vault PKI issuer** | ✗ | ✓ | Planned V2.1 (free) |
+| **DigiCert issuer** | ✗ | ✓ | Implemented (Beta) |
+| **Vault PKI issuer** | ✗ | ✓ | Implemented (Beta) |
 
 ---
 

docs/testing-guide.md

@@ -44,6 +44,9 @@ Comprehensive manual testing playbook. Every test has a concrete command, an exp
 - [Part 37: GUI Completeness (Pre-2.1.0-E)](#part-37-gui-completeness-pre-210-e)
 - [Part 38: Vault PKI Connector (M32)](#part-38-vault-pki-connector-m32)
 - [Part 39: DigiCert Connector (M37)](#part-39-digicert-connector-m37)
+- [Part 40: Issuer Catalog Page (M33)](#part-40-issuer-catalog-page-m33)
+- [Part 41: Frontend Audit Fixes](#part-41-frontend-audit-fixes)
+- [Part 42: IIS Target Connector (M39)](#part-42-iis-target-connector-m39)
 - [Release Sign-Off](#release-sign-off)
 
 ---
@@ -5372,6 +5375,320 @@ curl -s -X POST -H "$AUTH" \
 
 ---
 
+## Part 40: Issuer Catalog Page (M33)
+
+Frontend-only milestone. No backend changes. All tests are automated via `qa-smoke-test.sh` and `vitest`.
+
+### 40.1 Shared Issuer Type Config
+
+**Test:** Verify shared config file exists with all 6 supported types + 2 coming soon stubs.
+
+```bash
+test -f web/src/config/issuerTypes.ts
+grep -c 'VaultPKI' web/src/config/issuerTypes.ts    # >= 1
+grep -c 'DigiCert' web/src/config/issuerTypes.ts     # >= 1
+grep -cE 'eab_kid|eab_hmac' web/src/config/issuerTypes.ts  # >= 1
+grep -c 'sensitive' web/src/config/issuerTypes.ts     # >= 1
+```
+
+**PASS if** file exists, all types present, EAB fields and sensitive flags included.
+
+### 40.2 Composable Wizard Components
+
+**Test:** Verify reusable components exist.
+
+```bash
+test -f web/src/components/issuer/TypeSelector.tsx
+test -f web/src/components/issuer/ConfigForm.tsx
+test -f web/src/components/issuer/ConfigDetailModal.tsx
+```
+
+**PASS if** all 3 component files exist.
+
+### 40.3 Frontend Build
+
+**Test:** Verify frontend builds with zero errors.
+
+```bash
+cd web && npm run build 2>&1 | tail -1 | grep -q 'built in'
+```
+
+**PASS if** build succeeds.
+
+### 40.4 Frontend Tests
+
+**Test:** Verify all Vitest tests pass including new VaultPKI/DigiCert create tests.
+
+```bash
+cd web && npx vitest run 2>&1 | grep -qE 'Tests.*passed'
+```
+
+**PASS if** all tests pass.
+
+### 40.5 (Manual) Create VaultPKI Issuer via Wizard
+
+**Test:** Open Issuers page, click "Configure" on Vault PKI card, fill in form (addr, token, mount, role, ttl), submit.
+**PASS if** issuer appears in configured issuers table.
+
+### 40.6 (Manual) Create DigiCert Issuer via Wizard
+
+**Test:** Open Issuers page, click "Configure" on DigiCert card, fill in form (api_key, org_id, product_type), submit.
+**PASS if** issuer appears in configured issuers table.
+
+### 40.7 (Manual) Create ACME Issuer with EAB Fields
+
+**Test:** Open create wizard, select ACME, verify EAB Key ID and EAB HMAC Key fields are visible.
+**PASS if** EAB fields render and accept input.
+
+### 40.8 (Manual) Catalog Cards Show Correct Status
+
+**Test:** Verify catalog cards show "Connected" (green, count) for types with configured issuers, "Available" (blue) for unconfigured types, and "Coming Soon" (grey) for Sectigo/Entrust.
+**PASS if** all 8 cards render with correct status.
+
+### 40.9 (Manual) Config Detail Modal Shows Full Redacted Config
+
+**Test:** Click "View Config" on a configured issuer row. Verify modal shows full config JSON with sensitive fields (token, key, hmac, password, private, secret) redacted as `********`.
+**PASS if** modal opens, full config visible, sensitive fields redacted.
+
+### 40.10 (Manual) Issuer Type Filter Works
+
+**Test:** Use the type filter dropdown above the configured issuers table. Select a specific type.
+**PASS if** table filters to show only issuers of the selected type.
+
+---
+
+## Part 41: Frontend Audit Fixes
+
+Comprehensive frontend coverage audit closed 60 gaps between backend capabilities and GUI surfaces. This part validates the critical fixes.
+
+### Automated Tests (qa-smoke-test.sh Part 41)
+
+| # | Test | Assertion |
+|---|------|-----------|
+| 41.1 | Certificate TS type has lifecycle fields | `types.ts` contains `last_renewal_at`, `last_deployment_at`, `target_ids` |
+| 41.2 | API client has new endpoint functions | `client.ts` exports `updateIssuer`, `updateTarget`, `getCertificateDeployments`, `getCRL`, `getOCSPStatus`, `getPolicy` |
+| 41.3 | CertificatesPage has filter dropdowns | Contains `issuerFilter`, `ownerFilter`, `profileFilter` state vars |
+| 41.4 | CertificatesPage shows last_renewal_at | Column renders `last_renewal_at` field |
+| 41.5 | JobsPage shows error_message | Error column displays first 80 chars for failed jobs |
+| 41.6 | ProfilesPage has key algorithm fields | Create form includes `allowed_key_algorithms` with add/remove rows |
+| 41.7 | ProfilesPage has EKU checkboxes | Create form includes `allowed_ekus` checkbox group |
+| 41.8 | DiscoveryPage shows is_ca badge | CA badge renders for discovered CA certificates |
+| 41.9 | TargetDetailPage has Edit functionality | Edit button wired to `updateTarget` API call |
+| 41.10 | CertificatesPage has tags field | Create form includes tags input (key=value pairs) |
+| 41.11 | AgentFleetPage maps darwin to macOS | OS display mapping applied to pie chart and platform headers |
+| 41.12 | Frontend builds after audit fixes | `npm run build` succeeds |
+
+### Manual Tests
+
+**41.M1: Profile Create Form — Key Algorithm Configuration**
+
+1. Navigate to Profiles page, click "+ New Profile"
+2. Verify default algorithms shown: ECDSA 256+, RSA 2048+
+3. Click "Remove" on RSA row — verify it disappears
+4. Click "+ Add" — verify Ed25519 appears (with "fixed" instead of size dropdown)
+5. Submit form, verify profile created with correct `allowed_key_algorithms` array
+
+**PASS if** algorithms are configurable and persisted correctly.
+
+**41.M2: Profile Create Form — EKU Selection**
+
+1. In Create Profile modal, verify EKU checkboxes visible (serverAuth checked by default)
+2. Check "Email Protection (S/MIME)" and "Client Authentication"
+3. Submit, verify profile has `allowed_ekus: ["serverAuth", "emailProtection", "clientAuth"]`
+
+**PASS if** EKUs are selectable and sent to backend.
+
+**41.M3: Certificate Create Form — Tags**
+
+1. Navigate to Certificates page, click "+ New Certificate"
+2. Enter tags: `env=prod, team=platform, app=api`
+3. Submit, verify certificate created with `tags: {"env": "prod", "team": "platform", "app": "api"}`
+
+**PASS if** tags are parsed and persisted as key-value pairs.
+
+**41.M4: Jobs Table — Error Message Column**
+
+1. Navigate to Jobs page, filter to "Failed" status
+2. Verify "Error" column shows truncated error message (max 80 chars with "...")
+3. Hover over truncated message, verify full text in tooltip
+
+**PASS if** error messages visible for failed jobs.
+
+**41.M5: Certificates Table — Lifecycle Columns**
+
+1. Navigate to Certificates page
+2. Verify "Last Renewal" and "Last Deploy" columns visible
+3. Verify dates shown for certs with data, "—" for certs without
+
+**PASS if** lifecycle timestamps displayed.
+
+**41.M6: Certificate Filters — Issuer/Owner/Profile Dropdowns**
+
+1. Navigate to Certificates page
+2. Verify Issuer, Owner, Profile dropdown filters visible
+3. Select an issuer — verify table filters to matching certificates
+4. Clear filter, select a profile — verify filtering works
+
+**PASS if** all three filter dropdowns functional.
+
+**41.M7: Target Detail — Edit Button**
+
+1. Navigate to a target detail page
+2. Click "Edit" button
+3. Modify name, click "Save"
+4. Verify name updated on the page
+
+**PASS if** target edit persists via API.
+
+**41.M8: Discovery Table — CA Badge**
+
+1. Navigate to Discovery page
+2. Verify "Key" column shows algorithm + key size
+3. For CA certificates, verify purple "CA" badge displayed
+
+**PASS if** CA certificates visually distinguished.
+
+**41.M9: Fleet Overview — macOS Display**
+
+1. Navigate to Fleet Overview page
+2. Verify OS pie chart shows "macOS" instead of "darwin"
+3. Verify platform section headers show "macOS / amd64" (not "darwin / amd64")
+
+**PASS if** darwin correctly mapped to macOS in all locations.
+
+---
+
+## Part 42: IIS Target Connector (M39)
+
+The IIS target connector (M39) brings Windows infrastructure lifecycle management to certctl. Dual-mode implementation: agent-local PowerShell (primary) for servers with certctl agent, proxy agent WinRM for agentless Windows targets. Full test suite (28 tests) with mock executor pattern for cross-platform testing. Supports PEM-to-PFX conversion, SHA-1 thumbprint computation, and parameterized PowerShell execution.
+
+### Test Suite Coverage
+
+| Layer | Test Count | Focus | Cross-Platform |
+|-------|-----------|-------|-----------------|
+| ValidateConfig | 9 | Field validation, defaults, regex enforcement | Yes |
+| DeployCertificate | 7 | PFX conversion, script execution, error handling | Yes |
+| ValidateDeployment | 5 | Thumbprint verification, binding checks | Mock executor |
+| PFX Conversion | 4 | Certificate chain handling, password generation | Yes |
+| Helpers | 3 | Thumbprint computation, Windows time conversion | Yes |
+| **Total** | **28** | | **26 pass, 2 skip on non-Windows** |
+
+### Automated Tests (qa-smoke-test.sh Part 42)
+
+| # | Test | Assertion |
+|---|------|-----------|
+| 42.1 | IIS connector imports without error | `internal/connector/target/iis/` builds cleanly |
+| 42.2 | ValidateConfig rejects missing hostname | Validation fails when `hostname` absent |
+| 42.3 | ValidateConfig rejects missing site_name | Validation fails when `site_name` absent |
+| 42.4 | ValidateConfig applies defaults | `port` defaults to 443, `ip_address` to "*" |
+| 42.5 | ValidateConfig validates field regex | Rejects field names with invalid characters |
+| 42.6 | PEM-to-PFX conversion succeeds | PKCS#12 bundle created with random password |
+| 42.7 | SHA-1 thumbprint computed correctly | Matches Go crypto/sha1 output, hex-encoded |
+| 42.8 | PowerShell script is parameterized | No unescaped interpolation in generated commands |
+| 42.9 | Mock executor pattern works cross-platform | Tests pass on Linux/macOS via mock executor |
+| 42.10 | DeployCertificate calls Import-PfxCertificate | PowerShell command includes correct cert store |
+| 42.11 | DeployCertificate calls Set-WebBinding | PowerShell command includes site name + thumbprint |
+| 42.12 | ValidateDeployment executes Get-IISSiteBinding | Thumbprint comparison happens post-deployment |
+| 42.13 | Error cases logged and propagated | TLS verify failure, script timeout errors handled |
+| 42.14 | Windows time conversion helpers work | FileTime ↔ time.Time round-trip accurate |
+
+### Manual Tests (Windows Only)
+
+These tests require a real Windows Server 2019+ environment with IIS 10+. Skip on non-Windows platforms.
+
+**42.M1: Agent-Local Deployment — Happy Path**
+
+1. Provision a Windows Server 2019+ VM with IIS installed
+2. Download and install certctl-agent binary for windows-amd64
+3. Register agent with certctl server via heartbeat endpoint
+4. Create IIS target in certctl dashboard:
+   ```json
+   {
+     "hostname": "iis-server.local",
+     "site_name": "Default Web Site",
+     "cert_store": "WebHosting",
+     "port": 443,
+     "sni": true,
+     "ip_address": "*"
+   }
+   ```
+5. Issue a certificate (e.g., via Local CA)
+6. Create deployment job targeting the IIS target
+7. Agent polls work endpoint, executes PowerShell
+8. Verify on IIS: `Get-IISSiteBinding` shows new binding with correct thumbprint
+9. Verify in dashboard: Deployment job shows status=Completed, verified_at timestamp present
+
+**PASS if** certificate deployed to IIS binding with matching thumbprint, deployment job shows Completed with verification success.
+
+**42.M2: Agent-Local Deployment — Renewal**
+
+1. On the same IIS target, trigger renewal of the certificate
+2. Verify old certificate remains bound during renewal (until new one succeeds)
+3. Verify new certificate is imported and bound after deployment
+4. Verify old binding removed or updated in IIS
+
+**PASS if** renewal completes without downtime, old binding replaced with new.
+
+**42.M3: PFX Import to WebHosting Store**
+
+1. Manually generate a test PKCS#12 certificate
+2. Via certctl-agent on Windows, verify PowerShell can import to WebHosting store:
+   ```powershell
+   $pfx = New-Object System.Security.Cryptography.X509Certificates.X509Certificate2
+   $pfx.Import([System.IO.File]::ReadAllBytes("C:\temp\test.pfx"), $password, "Exportable")
+   $store = New-Object System.Security.Cryptography.X509Certificates.X509Store("WebHosting", "LocalMachine")
+   $store.Open("MaxAllowed")
+   $store.Add($pfx)
+   ```
+3. Verify certificate appears in IIS Certificate Manager
+
+**PASS if** certificate imports to WebHosting store successfully.
+
+**42.M4: Binding Verification — Thumbprint Match**
+
+1. Deploy a certificate to an IIS site via certctl
+2. Manually run on IIS server:
+   ```powershell
+   Get-IISSiteBinding -Name "Default Web Site" | Select-Object Thumbprint
+   ```
+3. Verify thumbprint matches certificate's SHA-1 hash (as shown in certctl GUI)
+
+**PASS if** thumbprints match exactly (hex-encoded, no colons).
+
+**42.M5: Error Handling — Invalid Site Name**
+
+1. Create IIS target with non-existent site name (e.g., "NonExistentSite")
+2. Trigger deployment
+3. Verify job fails with error message about invalid site
+4. Verify error is logged in agent and audit trail
+
+**PASS if** error handled gracefully, job marked Failed with reason.
+
+**42.M6: Field Validation — Config Injection Attempt**
+
+1. Try to create IIS target with site_name containing PowerShell metacharacters:
+   ```json
+   {
+     "site_name": "Default Web Site'; Get-Process; #"
+   }
+   ```
+2. Verify regex validation rejects this (field validation error, not API error)
+3. Verify no PowerShell execution occurs
+
+**PASS if** injection attempt blocked by field validation.
+
+**42.M7: SNI vs Non-SNI Binding**
+
+1. Create two IIS targets: one with `sni: true`, one with `sni: false`
+2. Deploy certificates to both
+3. Verify Set-WebBinding with `-SslFlags 1` (SNI) for first target
+4. Verify Set-WebBinding without SslFlags (no SNI) for second target
+5. Test TLS connection to both sites, verify SNI-enabled site handles multiple domains correctly
+
+**PASS if** SNI bindings configured correctly per target config.
+
+---
+
 ## Release Sign-Off
 
 All tests below must pass before tagging v2.1.0. Each row is one individual test from the guide above. The **Method** column indicates whether `qa-smoke-test.sh` covers the test automatically (**Auto**) or requires hands-on verification (**Manual**).
@@ -5952,14 +6269,60 @@ These must be green before starting manual QA:
 | 39.4 | Async poll behavior | Manual | ☐ |  | Requires DigiCert sandbox |
 | 39.5 | Revocation records locally | Manual | ☐ |  | Requires DigiCert sandbox |
 
+### Part 40: Issuer Catalog Page (M33)
+
+| Test | Description | Method | Pass? | Date | Notes |
+|------|-------------|--------|-------|------|-------|
+| 40.s1 | Shared issuerTypes config exists | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.1 |
+| 40.s2 | VaultPKI in issuerTypes config | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.2 |
+| 40.s3 | DigiCert in issuerTypes config | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.3 |
+| 40.s4 | ACME EAB fields in config | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.4 |
+| 40.s5 | Sensitive field flag in config | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.5 |
+| 40.s6 | ConfigDetailModal component exists | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.6 |
+| 40.s7 | Frontend build succeeds | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.7 |
+| 40.s8 | Frontend tests pass | Auto | ☑ | 2026-03-30 | qa-smoke-test.sh 40.8 |
+| 40.m1 | Create VaultPKI issuer via wizard | Manual | ☐ |  | |
+| 40.m2 | Create DigiCert issuer via wizard | Manual | ☐ |  | |
+| 40.m3 | Create ACME issuer with EAB fields | Manual | ☐ |  | |
+| 40.m4 | Catalog cards show correct status | Manual | ☐ |  | |
+| 40.m5 | Config detail modal shows full redacted config | Manual | ☐ |  | |
+| 40.m6 | Issuer type filter works | Manual | ☐ |  | |
+
+### Part 41: Frontend Audit Fixes
+
+| Test | Description | Method | Pass? | Date | Notes |
+|------|-------------|--------|-------|------|-------|
+| 41.s1 | Certificate TS type has lifecycle fields | Auto | ☐ |  | qa-smoke-test.sh 41.1 |
+| 41.s2 | API client has new endpoint functions | Auto | ☐ |  | qa-smoke-test.sh 41.2 |
+| 41.s3 | CertificatesPage has filter dropdowns | Auto | ☐ |  | qa-smoke-test.sh 41.3 |
+| 41.s4 | CertificatesPage shows last_renewal_at | Auto | ☐ |  | qa-smoke-test.sh 41.4 |
+| 41.s5 | JobsPage shows error_message | Auto | ☐ |  | qa-smoke-test.sh 41.5 |
+| 41.s6 | ProfilesPage has key algorithm fields | Auto | ☐ |  | qa-smoke-test.sh 41.6 |
+| 41.s7 | ProfilesPage has EKU checkboxes | Auto | ☐ |  | qa-smoke-test.sh 41.7 |
+| 41.s8 | DiscoveryPage shows is_ca badge | Auto | ☐ |  | qa-smoke-test.sh 41.8 |
+| 41.s9 | TargetDetailPage has Edit functionality | Auto | ☐ |  | qa-smoke-test.sh 41.9 |
+| 41.s10 | CertificatesPage has tags field | Auto | ☐ |  | qa-smoke-test.sh 41.10 |
+| 41.s11 | AgentFleetPage maps darwin to macOS | Auto | ☐ |  | qa-smoke-test.sh 41.11 |
+| 41.s12 | Frontend builds after audit fixes | Auto | ☐ |  | qa-smoke-test.sh 41.12 |
+| 41.m1 | Profile create form — key algorithm config | Manual | ☐ |  | |
+| 41.m2 | Profile create form — EKU selection | Manual | ☐ |  | |
+| 41.m3 | Certificate create form — tags | Manual | ☐ |  | |
+| 41.m4 | Jobs table — error message column | Manual | ☐ |  | |
+| 41.m5 | Certificates table — lifecycle columns | Manual | ☐ |  | |
+| 41.m6 | Certificate filters — issuer/owner/profile | Manual | ☐ |  | |
+| 41.m7 | Target detail — edit button | Manual | ☐ |  | |
+| 41.m8 | Discovery table — CA badge | Manual | ☐ |  | |
+| 41.m9 | Fleet overview — macOS display | Manual | ☐ |  | |
+
 ### Summary
 
 | Category | Count |
 |----------|-------|
-| ☑ Auto (passed in `qa-smoke-test.sh`) | 136 |
+| ☑ Auto (passed in `qa-smoke-test.sh`) | 144 |
+| ☐ Auto (not yet run) | 12 |
 | — Skipped (preconditions not met in demo) | 5 |
-| ☐ Manual (requires hands-on verification) | 226 |
-| **Total** | **367** |
+| ☐ Manual (requires hands-on verification) | 241 |
+| **Total** | **402** |
 
 **Automated tests must also be green.** CI passing is necessary but not sufficient — this manual QA catches integration issues that isolated unit tests miss.
 

go.mod

@@ -9,12 +9,19 @@ require (
 	github.com/testcontainers/testcontainers-go v0.35.0
 )
 
-require golang.org/x/crypto v0.31.0
+require (
+	golang.org/x/crypto v0.31.0
+	software.sslmate.com/src/go-pkcs12 v0.7.0
+)
 
 require (
 	dario.cat/mergo v1.0.0 // indirect
 	github.com/Azure/go-ansiterm v0.0.0-20210617225240-d185dfc1b5a1 // indirect
+	github.com/Azure/go-ntlmssp v0.0.0-20221128193559-754e69321358 // indirect
+	github.com/ChrisTrenkamp/goxpath v0.0.0-20210404020558-97928f7e12b6 // indirect
 	github.com/Microsoft/go-winio v0.6.2 // indirect
+	github.com/bodgit/ntlmssp v0.0.0-20240506230425-31973bb52d9b // indirect
+	github.com/bodgit/windows v1.0.1 // indirect
 	github.com/cenkalti/backoff/v4 v4.2.1 // indirect
 	github.com/containerd/containerd v1.7.18 // indirect
 	github.com/containerd/log v0.1.0 // indirect
@@ -29,12 +36,23 @@ require (
 	github.com/go-logr/logr v1.4.1 // indirect
 	github.com/go-logr/stdr v1.2.2 // indirect
 	github.com/go-ole/go-ole v1.2.6 // indirect
+	github.com/gofrs/uuid v4.4.0+incompatible // indirect
 	github.com/gogo/protobuf v1.3.2 // indirect
 	github.com/google/jsonschema-go v0.4.2 // indirect
+	github.com/hashicorp/go-cleanhttp v0.5.2 // indirect
+	github.com/hashicorp/go-uuid v1.0.3 // indirect
+	github.com/jcmturner/aescts/v2 v2.0.0 // indirect
+	github.com/jcmturner/dnsutils/v2 v2.0.0 // indirect
+	github.com/jcmturner/gofork v1.7.6 // indirect
+	github.com/jcmturner/goidentity/v6 v6.0.1 // indirect
+	github.com/jcmturner/gokrb5/v8 v8.4.4 // indirect
+	github.com/jcmturner/rpc/v2 v2.0.3 // indirect
 	github.com/klauspost/compress v1.17.4 // indirect
 	github.com/kr/text v0.2.0 // indirect
 	github.com/lufia/plan9stats v0.0.0-20211012122336-39d0f177ccd0 // indirect
 	github.com/magiconair/properties v1.8.7 // indirect
+	github.com/masterzen/simplexml v0.0.0-20190410153822-31eea3082786 // indirect
+	github.com/masterzen/winrm v0.0.0-20250927112105-5f8e6c707321 // indirect
 	github.com/moby/docker-image-spec v1.3.1 // indirect
 	github.com/moby/patternmatcher v0.6.0 // indirect
 	github.com/moby/sys/sequential v0.5.0 // indirect
@@ -52,6 +70,7 @@ require (
 	github.com/shoenig/go-m1cpu v0.1.6 // indirect
 	github.com/sirupsen/logrus v1.9.3 // indirect
 	github.com/stretchr/testify v1.9.0 // indirect
+	github.com/tidwall/transform v0.0.0-20201103190739-32f242e2dbde // indirect
 	github.com/tklauser/go-sysconf v0.3.12 // indirect
 	github.com/tklauser/numcpus v0.6.1 // indirect
 	github.com/yosida95/uritemplate/v3 v3.0.2 // indirect
@@ -60,8 +79,9 @@ require (
 	go.opentelemetry.io/otel v1.24.0 // indirect
 	go.opentelemetry.io/otel/metric v1.24.0 // indirect
 	go.opentelemetry.io/otel/trace v1.24.0 // indirect
+	golang.org/x/net v0.23.0 // indirect
 	golang.org/x/oauth2 v0.34.0 // indirect
 	golang.org/x/sys v0.40.0 // indirect
+	golang.org/x/text v0.21.0 // indirect
 	gopkg.in/yaml.v3 v3.0.1 // indirect
-	software.sslmate.com/src/go-pkcs12 v0.7.0 // indirect
 )

go.sum

@@ -4,8 +4,16 @@ github.com/AdaLogics/go-fuzz-headers v0.0.0-20230811130428-ced1acdcaa24 h1:bvDV9
 github.com/AdaLogics/go-fuzz-headers v0.0.0-20230811130428-ced1acdcaa24/go.mod h1:8o94RPi1/7XTJvwPpRSzSUedZrtlirdB3r9Z20bi2f8=
 github.com/Azure/go-ansiterm v0.0.0-20210617225240-d185dfc1b5a1 h1:UQHMgLO+TxOElx5B5HZ4hJQsoJ/PvUvKRhJHDQXO8P8=
 github.com/Azure/go-ansiterm v0.0.0-20210617225240-d185dfc1b5a1/go.mod h1:xomTg63KZ2rFqZQzSB4Vz2SUXa1BpHTVz9L5PTmPC4E=
+github.com/Azure/go-ntlmssp v0.0.0-20221128193559-754e69321358 h1:mFRzDkZVAjdal+s7s0MwaRv9igoPqLRdzOLzw/8Xvq8=
+github.com/Azure/go-ntlmssp v0.0.0-20221128193559-754e69321358/go.mod h1:chxPXzSsl7ZWRAuOIE23GDNzjWuZquvFlgA8xmpunjU=
+github.com/ChrisTrenkamp/goxpath v0.0.0-20210404020558-97928f7e12b6 h1:w0E0fgc1YafGEh5cROhlROMWXiNoZqApk2PDN0M1+Ns=
+github.com/ChrisTrenkamp/goxpath v0.0.0-20210404020558-97928f7e12b6/go.mod h1:nuWgzSkT5PnyOd+272uUmV0dnAnAn42Mk7PiQC5VzN4=
 github.com/Microsoft/go-winio v0.6.2 h1:F2VQgta7ecxGYO8k3ZZz3RS8fVIXVxONVUPlNERoyfY=
 github.com/Microsoft/go-winio v0.6.2/go.mod h1:yd8OoFMLzJbo9gZq8j5qaps8bJ9aShtEA8Ipt1oGCvU=
+github.com/bodgit/ntlmssp v0.0.0-20240506230425-31973bb52d9b h1:baFN6AnR0SeC194X2D292IUZcHDs4JjStpqtE70fjXE=
+github.com/bodgit/ntlmssp v0.0.0-20240506230425-31973bb52d9b/go.mod h1:Ram6ngyPDmP+0t6+4T2rymv0w0BS9N8Ch5vvUJccw5o=
+github.com/bodgit/windows v1.0.1 h1:tF7K6KOluPYygXa3Z2594zxlkbKPAOvqr97etrGNIz4=
+github.com/bodgit/windows v1.0.1/go.mod h1:a6JLwrB4KrTR5hBpp8FI9/9W9jJfeQ2h4XDXU74ZCdM=
 github.com/cenkalti/backoff/v4 v4.2.1 h1:y4OZtCnogmCPw98Zjyt5a6+QwPLGkiQsYW5oUqylYbM=
 github.com/cenkalti/backoff/v4 v4.2.1/go.mod h1:Y3VNntkOUPxTVeUxJ/G5vcM//AlwfmyYozVcomhLiZE=
 github.com/containerd/containerd v1.7.18 h1:jqjZTQNfXGoEaZdW1WwPU0RqSn1Bm2Ay/KJPUuO8nao=
@@ -39,6 +47,8 @@ github.com/go-logr/stdr v1.2.2 h1:hSWxHoqTgW2S2qGc0LTAI563KZ5YKYRhT3MFKZMbjag=
 github.com/go-logr/stdr v1.2.2/go.mod h1:mMo/vtBO5dYbehREoey6XUKy/eSumjCCveDpRre4VKE=
 github.com/go-ole/go-ole v1.2.6 h1:/Fpf6oFPoeFik9ty7siob0G6Ke8QvQEuVcuChpwXzpY=
 github.com/go-ole/go-ole v1.2.6/go.mod h1:pprOEPIfldk/42T2oK7lQ4v4JSDwmV0As9GaiUsvbm0=
+github.com/gofrs/uuid v4.4.0+incompatible h1:3qXRTX8/NbyulANqlc0lchS1gqAVxRgsuW1YrTJupqA=
+github.com/gofrs/uuid v4.4.0+incompatible/go.mod h1:b2aQJv3Z4Fp6yNu3cdSllBxTCLRxnplIgP/c0N/04lM=
 github.com/gogo/protobuf v1.3.2 h1:Ov1cvc58UF3b5XjBnZv7+opcTcQFZebYjWzi34vdm4Q=
 github.com/gogo/protobuf v1.3.2/go.mod h1:P1XiOD3dCwIKUDQYPy72D8LYyHL2YPYrpS2s69NZV8Q=
 github.com/golang-jwt/jwt/v5 v5.3.0 h1:pv4AsKCKKZuqlgs5sUmn4x8UlGa0kEVt/puTpKx9vvo=
@@ -52,8 +62,27 @@ github.com/google/jsonschema-go v0.4.2 h1:tmrUohrwoLZZS/P3x7ex0WAVknEkBZM46iALbc
 github.com/google/jsonschema-go v0.4.2/go.mod h1:r5quNTdLOYEz95Ru18zA0ydNbBuYoo9tgaYcxEYhJVE=
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+github.com/gorilla/securecookie v1.1.1/go.mod h1:ra0sb63/xPlUeL+yeDciTfxMRAA+MP+HVt/4epWDjd4=
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 github.com/grpc-ecosystem/grpc-gateway/v2 v2.16.0 h1:YBftPWNWd4WwGqtY2yeZL2ef8rHAxPBD8KFhJpmcqms=
 github.com/grpc-ecosystem/grpc-gateway/v2 v2.16.0/go.mod h1:YN5jB8ie0yfIUg6VvR9Kz84aCaG7AsGZnLjhHbUqwPg=
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 github.com/kisielk/errcheck v1.5.0/go.mod h1:pFxgyoBC7bSaBwPgfKdkLd5X25qrDl4LWUI2bnpBCr8=
 github.com/kisielk/gotool v1.0.0/go.mod h1:XhKaO+MFFWcvkIS/tQcRk01m1F5IRFswLeQ+oQHNcck=
 github.com/klauspost/compress v1.17.4 h1:Ej5ixsIri7BrIjBkRZLTo6ghwrEtHFk7ijlczPW4fZ4=
@@ -68,6 +97,10 @@ github.com/lufia/plan9stats v0.0.0-20211012122336-39d0f177ccd0 h1:6E+4a0GO5zZEnZ
 github.com/lufia/plan9stats v0.0.0-20211012122336-39d0f177ccd0/go.mod h1:zJYVVT2jmtg6P3p1VtQj7WsuWi/y4VnjVBn7F8KPB3I=
 github.com/magiconair/properties v1.8.7 h1:IeQXZAiQcpL9mgcAe1Nu6cX9LLw6ExEHKjN0VQdvPDY=
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+github.com/masterzen/simplexml v0.0.0-20190410153822-31eea3082786/go.mod h1:kCEbxUJlNDEBNbdQMkPSp6yaKcRXVI6f4ddk8Riv4bc=
+github.com/masterzen/winrm v0.0.0-20250927112105-5f8e6c707321 h1:AKIJL2PfBX2uie0Mn5pxtG1+zut3hAVMZbRfoXecFzI=
+github.com/masterzen/winrm v0.0.0-20250927112105-5f8e6c707321/go.mod h1:JajVhkiG2bYSNYYPYuWG7WZHr42CTjMTcCjfInRNCqc=
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@@ -111,14 +144,18 @@ github.com/stretchr/objx v0.4.0/go.mod h1:YvHI0jy2hoMjB+UWwv71VJQ9isScKT/TqJzVSS
 github.com/stretchr/objx v0.5.0/go.mod h1:Yh+to48EsGEfYuaHDzXPcE3xhTkx73EhmCGUpEOglKo=
 github.com/stretchr/objx v0.5.2 h1:xuMeJ0Sdp5ZMRXx/aWO6RZxdr3beISkG5/G/aIRr3pY=
 github.com/stretchr/objx v0.5.2/go.mod h1:FRsXN1f5AsAjCGJKqEizvkpNtU+EGNCLh3NxZ/8L+MA=
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 github.com/stretchr/testify v1.9.0/go.mod h1:r2ic/lqez/lEtzL7wO/rwa5dbSLXVDPFyf8C91i36aY=
 github.com/testcontainers/testcontainers-go v0.35.0 h1:uADsZpTKFAtp8SLK+hMwSaa+X+JiERHtd4sQAFmXeMo=
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@@ -127,6 +164,7 @@ github.com/yosida95/uritemplate/v3 v3.0.2 h1:Ed3Oyj9yrmi9087+NczuL5BwkIc4wvTb5zI
 github.com/yosida95/uritemplate/v3 v3.0.2/go.mod h1:ILOh0sOhIJR3+L/8afwt/kE++YT040gmv5BQTMR2HP4=
 github.com/yuin/goldmark v1.1.27/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9decYSb74=
 github.com/yuin/goldmark v1.2.1/go.mod h1:3hX8gzYuyVAZsxl0MRgGTJEmQBFcNTphYh9decYSb74=
+github.com/yuin/goldmark v1.4.13/go.mod h1:6yULJ656Px+3vBD8DxQVa3kxgyrAnzto9xy5taEt/CY=
 github.com/yusufpapurcu/wmi v1.2.3 h1:E1ctvB7uKFMOJw3fdOW32DwGE9I7t++CRUEMKvFoFiw=
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 go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp v0.49.0 h1:jq9TW8u3so/bN+JPT166wjOI6/vQPF6Xe7nMNIltagk=
@@ -148,14 +186,22 @@ go.opentelemetry.io/proto/otlp v1.0.0/go.mod h1:Sy6pihPLfYHkr3NkUbEhGHFhINUSI/v8
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20191011191535-87dc89f01550/go.mod h1:yigFU9vqHzYiE8UmvKecakEJjdnWj3jj499lnFckfCI=
 golang.org/x/crypto v0.0.0-20200622213623-75b288015ac9/go.mod h1:LzIPMQfyMNhhGPhUkYOs5KpL4U8rLKemX1yGLhDgUto=
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+golang.org/x/crypto v0.6.0/go.mod h1:OFC/31mSvZgRz0V1QTNCzfAI1aIRzbiufJtkMIlEp58=
 golang.org/x/crypto v0.31.0 h1:ihbySMvVjLAeSH1IbfcRTkD/iNscyz8rGzjF/E5hV6U=
 golang.org/x/crypto v0.31.0/go.mod h1:kDsLvtWBEx7MV9tJOj9bnXsPbxwJQ6csT/x4KIN4Ssk=
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+golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4/go.mod h1:jJ57K6gSWd91VN4djpZkiMVwK6gcyfeH4XE8wZrZaV4=
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+golang.org/x/net v0.6.0/go.mod h1:2Tu9+aMcznHK/AK1HMvgo6xiTLG5rD5rZLDS+rp2Bjs=
+golang.org/x/net v0.7.0/go.mod h1:2Tu9+aMcznHK/AK1HMvgo6xiTLG5rD5rZLDS+rp2Bjs=
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@@ -163,22 +209,33 @@ golang.org/x/oauth2 v0.34.0/go.mod h1:lzm5WQJQwKZ3nwavOZ3IS5Aulzxi68dUSgRHujetwE
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@@ -187,6 +244,7 @@ golang.org/x/tools v0.0.0-20180917221912-90fa682c2a6e/go.mod h1:n7NCudcB/nEzxVGm
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+golang.org/x/tools v0.1.12/go.mod h1:hNGJHUnrk76NpqgfD5Aqm5Crs+Hm0VOH/i9J2+nxYbc=
 golang.org/x/tools v0.41.0 h1:a9b8iMweWG+S0OBnlU36rzLp20z1Rp10w+IY2czHTQc=
 golang.org/x/tools v0.41.0/go.mod h1:XSY6eDqxVNiYgezAVqqCeihT4j1U2CCsqvH3WhQpnlg=
 golang.org/x/xerrors v0.0.0-20190717185122-a985d3407aa7/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
@@ -205,6 +263,7 @@ google.golang.org/protobuf v1.33.0/go.mod h1:c6P6GXX6sHbq/GpV6MGZEdwhWPcYBgnhAHh
 gopkg.in/check.v1 v0.0.0-20161208181325-20d25e280405/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
 gopkg.in/check.v1 v1.0.0-20201130134442-10cb98267c6c h1:Hei/4ADfdWqJk1ZMxUNpqntNwaWcugrBjAiHlqqRiVk=
 gopkg.in/check.v1 v1.0.0-20201130134442-10cb98267c6c/go.mod h1:JHkPIbrfpd72SG/EVd6muEfDQjcINNoR0C8j2r3qZ4Q=
+gopkg.in/yaml.v2 v2.2.2/go.mod h1:hI93XBmqTisBFMUTm0b8Fm+jr3Dg1NNxqwp+5A1VGuI=
 gopkg.in/yaml.v3 v3.0.0-20200313102051-9f266ea9e77c/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=
 gopkg.in/yaml.v3 v3.0.1 h1:fxVm/GzAzEWqLHuvctI91KS9hhNmmWOoWu0XTYJS7CA=
 gopkg.in/yaml.v3 v3.0.1/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=

internal/api/handler/agents.go

@@ -252,6 +252,7 @@ func (h AgentHandler) AgentCSRSubmit(w http.ResponseWriter, r *http.Request) {
 	}
 
 	if err != nil {
+		slog.Error("CSR submission failed", "agent_id", agentID, "certificate_id", req.CertificateID, "error", err.Error())
 		ErrorWithRequestID(w, http.StatusInternalServerError, "Failed to submit CSR", requestID)
 		return
 	}
@@ -274,9 +275,10 @@ func (h AgentHandler) AgentCertificatePickup(w http.ResponseWriter, r *http.Requ
 	requestID := middleware.GetRequestID(r.Context())
 
 	// Extract agent ID and certificate ID from path /api/v1/agents/{id}/certificates/{cert_id}
+	// After TrimPrefix, path is "{id}/certificates/{cert_id}" → split gives [id, "certificates", cert_id]
 	path := strings.TrimPrefix(r.URL.Path, "/api/v1/agents/")
 	parts := strings.Split(path, "/")
-	if len(parts) < 4 || parts[0] == "" || parts[2] == "" {
+	if len(parts) < 3 || parts[0] == "" || parts[2] == "" {
 		ErrorWithRequestID(w, http.StatusBadRequest, "Agent ID and Certificate ID are required", requestID)
 		return
 	}

internal/api/handler/certificates.go

@@ -243,6 +243,7 @@ func (h CertificateHandler) CreateCertificate(w http.ResponseWriter, r *http.Req
 
 	created, err := h.svc.CreateCertificate(cert)
 	if err != nil {
+		slog.Error("failed to create certificate", "error", err, "request_id", requestID, "common_name", cert.CommonName, "name", cert.Name)
 		ErrorWithRequestID(w, http.StatusInternalServerError, "Failed to create certificate", requestID)
 		return
 	}

internal/api/handler/validation.go

@@ -3,6 +3,7 @@ package handler
 import (
 	"fmt"
 	"net"
+	"net/mail"
 	"strings"
 )
 
@@ -13,6 +14,7 @@ type ValidationError struct {
 }
 
 // ValidateCommonName validates a certificate common name.
+// Accepts hostnames (TLS), IP addresses, and email addresses (S/MIME).
 func ValidateCommonName(cn string) error {
 	if cn == "" {
 		return ValidationError{Field: "common_name", Message: "common_name is required"}
@@ -20,6 +22,13 @@ func ValidateCommonName(cn string) error {
 	if len(cn) > 253 {
 		return ValidationError{Field: "common_name", Message: "common_name must be 253 characters or fewer"}
 	}
+	// If CN contains @, validate as email address (S/MIME certificates)
+	if strings.Contains(cn, "@") {
+		if _, err := mail.ParseAddress(cn); err != nil {
+			return ValidationError{Field: "common_name", Message: fmt.Sprintf("invalid email format for S/MIME common name: %v", err)}
+		}
+		return nil
+	}
 	// Basic hostname validation: allow alphanumeric, dots, hyphens
 	if err := isValidHostname(cn); err != nil {
 		return ValidationError{Field: "common_name", Message: fmt.Sprintf("invalid hostname format: %v", err)}

internal/config/config.go

@@ -256,6 +256,11 @@ type ACMEConfig struct {
 	// Default: false. Requires a CA that supports ARI (e.g., Let's Encrypt).
 	// Setting: CERTCTL_ACME_ARI_ENABLED environment variable.
 	ARIEnabled bool
+
+	// Insecure skips TLS certificate verification when connecting to the ACME directory.
+	// Only use for testing with self-signed ACME servers like Pebble. Never in production.
+	// Setting: CERTCTL_ACME_INSECURE environment variable.
+	Insecure bool
 }
 
 // OpenSSLConfig contains OpenSSL/Custom CA issuer connector configuration.
@@ -503,6 +508,7 @@ func Load() (*Config, error) {
 			DNSCleanUpScript:       getEnv("CERTCTL_ACME_DNS_CLEANUP_SCRIPT", ""),
 			DNSPersistIssuerDomain: getEnv("CERTCTL_ACME_DNS_PERSIST_ISSUER_DOMAIN", ""),
 			ARIEnabled:             getEnvBool("CERTCTL_ACME_ARI_ENABLED", false),
+			Insecure:               getEnvBool("CERTCTL_ACME_INSECURE", false),
 		},
 		Digest: DigestConfig{
 			Enabled:    getEnvBool("CERTCTL_DIGEST_ENABLED", false),

internal/connector/issuer/acme/acme.go

@@ -5,6 +5,7 @@ import (
 	"crypto/ecdsa"
 	"crypto/elliptic"
 	"crypto/rand"
+	"crypto/tls"
 	"crypto/x509"
 	"encoding/base64"
 	"encoding/json"
@@ -58,6 +59,10 @@ type Config struct {
 	// ARIEnabled enables ACME Renewal Information (RFC 9702) support per CERTCTL_ACME_ARI_ENABLED.
 	// When enabled, the connector queries the CA's ARI endpoint to get CA-directed renewal timing.
 	ARIEnabled bool `json:"ari_enabled,omitempty"`
+
+	// Insecure skips TLS certificate verification when connecting to the ACME directory.
+	// Only use for testing with self-signed ACME servers like Pebble.
+	Insecure bool `json:"insecure,omitempty"`
 }
 
 // Connector implements the issuer.Connector interface for ACME-compatible CAs
@@ -114,6 +119,18 @@ func New(config *Config, logger *slog.Logger) *Connector {
 	return c
 }
 
+// httpClient returns an HTTP client configured for the ACME connector.
+// When Insecure is true (e.g., for Pebble test servers), TLS verification is skipped.
+func (c *Connector) httpClient() *http.Client {
+	client := &http.Client{Timeout: 30 * time.Second}
+	if c.config != nil && c.config.Insecure {
+		client.Transport = &http.Transport{
+			TLSClientConfig: &tls.Config{InsecureSkipVerify: true}, //nolint:gosec // Intentional for test ACME servers (Pebble)
+		}
+	}
+	return client
+}
+
 // ValidateConfig checks that the ACME directory URL is reachable and valid.
 func (c *Connector) ValidateConfig(ctx context.Context, rawConfig json.RawMessage) error {
 	var cfg Config
@@ -129,10 +146,16 @@ func (c *Connector) ValidateConfig(ctx context.Context, rawConfig json.RawMessag
 		return fmt.Errorf("ACME email is required")
 	}
 
-	c.logger.Info("validating ACME configuration", "directory_url", cfg.DirectoryURL)
+	c.logger.Info("validating ACME configuration", "directory_url", cfg.DirectoryURL, "insecure", cfg.Insecure)
+
+	// Apply config so httpClient() can use it for the directory probe.
+	// This persists across the function — if validation fails early, the config
+	// will still be set, but that's fine since a failed ValidateConfig means
+	// the connector won't be used.
+	c.config = &cfg
 
 	// Verify that the directory URL is reachable
-	httpClient := &http.Client{Timeout: 10 * time.Second}
+	httpClient := c.httpClient()
 	req, err := http.NewRequestWithContext(ctx, http.MethodGet, cfg.DirectoryURL, nil)
 	if err != nil {
 		return fmt.Errorf("failed to create request: %w", err)
@@ -203,6 +226,7 @@ func (c *Connector) ensureClient(ctx context.Context) error {
 	c.client = &acme.Client{
 		Key:          key,
 		DirectoryURL: c.config.DirectoryURL,
+		HTTPClient:   c.httpClient(),
 	}
 
 	// Register or retrieve the ACME account
@@ -338,6 +362,12 @@ func (c *Connector) IssueCertificate(ctx context.Context, request issuer.Issuanc
 	}
 	c.logger.Info("ACME order created", "order_url", order.URI, "status", order.Status)
 
+	// Save FinalizeURL and URI before WaitOrder — WaitOrder returns a new Order
+	// object that may have empty FinalizeURL and URI fields (Go's crypto/acme
+	// WaitOrder doesn't populate Order.URI on the returned struct).
+	finalizeURL := order.FinalizeURL
+	orderURI := order.URI
+
 	// Step 2: Solve authorizations (HTTP-01 challenges)
 	if order.Status == acme.StatusPending {
 		if err := c.solveAuthorizations(ctx, order.AuthzURLs); err != nil {
@@ -345,10 +375,18 @@ func (c *Connector) IssueCertificate(ctx context.Context, request issuer.Issuanc
 		}
 
 		// Wait for the order to be ready
-		order, err = c.client.WaitOrder(ctx, order.URI)
+		order, err = c.client.WaitOrder(ctx, orderURI)
 		if err != nil {
 			return nil, fmt.Errorf("order failed after challenge: %w", err)
 		}
+		// Update finalizeURL from the waited order if it has one
+		if order.FinalizeURL != "" {
+			finalizeURL = order.FinalizeURL
+		}
+		// Preserve orderURI — WaitOrder doesn't populate Order.URI
+		if order.URI != "" {
+			orderURI = order.URI
+		}
 	}
 
 	if order.Status != acme.StatusReady {
@@ -361,9 +399,39 @@ func (c *Connector) IssueCertificate(ctx context.Context, request issuer.Issuanc
 		return nil, fmt.Errorf("failed to parse CSR: %w", err)
 	}
 
-	derChain, _, err := c.client.CreateOrderCert(ctx, order.FinalizeURL, csrDER, true)
+	if finalizeURL == "" {
+		return nil, fmt.Errorf("ACME order has no finalize URL (order URI: %s, status: %s)", order.URI, order.Status)
+	}
+
+	// Step 3b: Finalize the order and fetch the certificate.
+	// CreateOrderCert POSTs the CSR to the finalize URL and attempts to retrieve
+	// the certificate. Some ACME servers (notably Pebble) return the order object
+	// per RFC 8555 rather than redirecting to the cert, which can cause
+	// CreateOrderCert's internal cert URL resolution to fail. In that case, we
+	// fall back to WaitOrder (to get the CertURL) + FetchCert.
+	derChain, _, err := c.client.CreateOrderCert(ctx, finalizeURL, csrDER, true)
 	if err != nil {
-		return nil, fmt.Errorf("failed to finalize order: %w", err)
+		c.logger.Warn("CreateOrderCert failed, attempting manual certificate fetch",
+			"error", err, "order_uri", orderURI)
+
+		// The finalize POST likely succeeded (the CA issued the cert) but cert
+		// retrieval failed. WaitOrder returns the order in "valid" state with
+		// CertURL populated.
+		validOrder, waitErr := c.client.WaitOrder(ctx, orderURI)
+		if waitErr != nil {
+			return nil, fmt.Errorf("failed to finalize order: %w (wait fallback: %v)", err, waitErr)
+		}
+
+		if validOrder.CertURL == "" {
+			return nil, fmt.Errorf("order finalized but no certificate URL returned (original error: %w)", err)
+		}
+
+		c.logger.Info("fetching certificate via fallback", "cert_url", validOrder.CertURL)
+		fetchedChain, fetchErr := c.client.FetchCert(ctx, validOrder.CertURL, true)
+		if fetchErr != nil {
+			return nil, fmt.Errorf("failed to fetch certificate: %w (original finalize error: %v)", fetchErr, err)
+		}
+		derChain = fetchedChain
 	}
 
 	if len(derChain) == 0 {
@@ -387,7 +455,7 @@ func (c *Connector) IssueCertificate(ctx context.Context, request issuer.Issuanc
 		Serial:    serial,
 		NotBefore: notBefore,
 		NotAfter:  notAfter,
-		OrderID:   order.URI,
+		OrderID:   orderURI,
 	}, nil
 }
 

internal/connector/issuer/stepca/jwe.go

@@ -0,0 +1,264 @@
+// Package stepca — JWE decryption for step-ca provisioner keys.
+//
+// step-ca stores provisioner private keys as JWE-encrypted JSON files using:
+//   - Algorithm: PBES2-HS256+A128KW (PBKDF2 key derivation + AES-128 Key Wrap)
+//   - Encryption: A128GCM (AES-128 in GCM mode)
+//
+// This file implements just enough JWE to decrypt these files without requiring
+// an external JOSE library. Uses only stdlib + golang.org/x/crypto/pbkdf2.
+package stepca
+
+import (
+	"crypto/aes"
+	"crypto/cipher"
+	"crypto/ecdsa"
+	"crypto/elliptic"
+	"crypto/sha256"
+	"encoding/base64"
+	"encoding/binary"
+	"encoding/json"
+	"fmt"
+	"math/big"
+
+	"golang.org/x/crypto/pbkdf2"
+)
+
+// jweJSON is the JWE JSON Serialization format used by step-ca provisioner keys.
+type jweJSON struct {
+	Protected    string `json:"protected"`
+	EncryptedKey string `json:"encrypted_key"`
+	IV           string `json:"iv"`
+	Ciphertext   string `json:"ciphertext"`
+	Tag          string `json:"tag"`
+}
+
+// jweHeader is the protected header inside a step-ca provisioner key JWE.
+type jweHeader struct {
+	Alg string `json:"alg"` // "PBES2-HS256+A128KW"
+	Enc string `json:"enc"` // "A128GCM"
+	Cty string `json:"cty"` // "jwk+json"
+	P2s string `json:"p2s"` // PBKDF2 salt (base64url)
+	P2c int    `json:"p2c"` // PBKDF2 iteration count
+}
+
+// jwkEC is a minimal JWK representation for EC private keys.
+type jwkEC struct {
+	Kty string `json:"kty"`
+	Crv string `json:"crv"`
+	X   string `json:"x"`
+	Y   string `json:"y"`
+	D   string `json:"d"`
+	Kid string `json:"kid"`
+}
+
+// decryptProvisionerKey decrypts a step-ca JWE-encrypted provisioner key file.
+// Returns the parsed ECDSA private key and the key ID (kid).
+func decryptProvisionerKey(jweData []byte, password string) (*ecdsa.PrivateKey, string, error) {
+	// Parse JWE JSON
+	var jwe jweJSON
+	if err := json.Unmarshal(jweData, &jwe); err != nil {
+		return nil, "", fmt.Errorf("failed to parse JWE JSON: %w", err)
+	}
+
+	// Decode protected header
+	headerBytes, err := base64.RawURLEncoding.DecodeString(jwe.Protected)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decode JWE protected header: %w", err)
+	}
+
+	var header jweHeader
+	if err := json.Unmarshal(headerBytes, &header); err != nil {
+		return nil, "", fmt.Errorf("failed to parse JWE header: %w", err)
+	}
+
+	if header.Alg != "PBES2-HS256+A128KW" {
+		return nil, "", fmt.Errorf("unsupported JWE algorithm: %s (expected PBES2-HS256+A128KW)", header.Alg)
+	}
+	if header.Enc != "A128GCM" && header.Enc != "A256GCM" {
+		return nil, "", fmt.Errorf("unsupported JWE encryption: %s (expected A128GCM or A256GCM)", header.Enc)
+	}
+
+	// Decode PBKDF2 salt
+	p2sSalt, err := base64.RawURLEncoding.DecodeString(header.P2s)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decode PBKDF2 salt: %w", err)
+	}
+
+	// Decode encrypted key, IV, ciphertext, tag
+	encryptedKey, err := base64.RawURLEncoding.DecodeString(jwe.EncryptedKey)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decode encrypted key: %w", err)
+	}
+
+	iv, err := base64.RawURLEncoding.DecodeString(jwe.IV)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decode IV: %w", err)
+	}
+
+	ciphertext, err := base64.RawURLEncoding.DecodeString(jwe.Ciphertext)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decode ciphertext: %w", err)
+	}
+
+	tag, err := base64.RawURLEncoding.DecodeString(jwe.Tag)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decode tag: %w", err)
+	}
+
+	// Step 1: Derive Key Encryption Key (KEK) using PBKDF2
+	// PBES2-HS256+A128KW: PBKDF2-SHA256, 16-byte derived key for AES-128 Key Wrap
+	// The salt for PBKDF2 is: UTF8(alg) || 0x00 || p2s
+	algBytes := []byte(header.Alg)
+	salt := make([]byte, len(algBytes)+1+len(p2sSalt))
+	copy(salt, algBytes)
+	salt[len(algBytes)] = 0x00
+	copy(salt[len(algBytes)+1:], p2sSalt)
+
+	kekSize := 16 // AES-128 for A128KW
+	kek := pbkdf2.Key([]byte(password), salt, header.P2c, kekSize, sha256.New)
+
+	// Step 2: AES Key Unwrap (RFC 3394) to get the Content Encryption Key (CEK)
+	cek, err := aesKeyUnwrap(kek, encryptedKey)
+	if err != nil {
+		return nil, "", fmt.Errorf("AES key unwrap failed (wrong password?): %w", err)
+	}
+
+	// Step 3: AES-GCM decrypt the payload
+	// AAD = ASCII(BASE64URL(protected header))
+	aad := []byte(jwe.Protected)
+
+	block, err := aes.NewCipher(cek)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to create AES cipher: %w", err)
+	}
+
+	gcm, err := cipher.NewGCM(block)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to create GCM: %w", err)
+	}
+
+	// GCM expects ciphertext+tag concatenated
+	sealed := append(ciphertext, tag...)
+	plaintext, err := gcm.Open(nil, iv, sealed, aad)
+	if err != nil {
+		return nil, "", fmt.Errorf("GCM decryption failed: %w", err)
+	}
+
+	// Step 4: Parse the decrypted JWK
+	var jwk jwkEC
+	if err := json.Unmarshal(plaintext, &jwk); err != nil {
+		return nil, "", fmt.Errorf("failed to parse decrypted JWK: %w", err)
+	}
+
+	if jwk.Kty != "EC" {
+		return nil, "", fmt.Errorf("unsupported JWK key type: %s (expected EC)", jwk.Kty)
+	}
+
+	key, err := jwkToECDSA(&jwk)
+	if err != nil {
+		return nil, "", err
+	}
+
+	return key, jwk.Kid, nil
+}
+
+// jwkToECDSA converts a JWK EC key to an *ecdsa.PrivateKey.
+func jwkToECDSA(jwk *jwkEC) (*ecdsa.PrivateKey, error) {
+	var curve elliptic.Curve
+	switch jwk.Crv {
+	case "P-256":
+		curve = elliptic.P256()
+	case "P-384":
+		curve = elliptic.P384()
+	case "P-521":
+		curve = elliptic.P521()
+	default:
+		return nil, fmt.Errorf("unsupported curve: %s", jwk.Crv)
+	}
+
+	xBytes, err := base64.RawURLEncoding.DecodeString(jwk.X)
+	if err != nil {
+		return nil, fmt.Errorf("failed to decode JWK x: %w", err)
+	}
+	yBytes, err := base64.RawURLEncoding.DecodeString(jwk.Y)
+	if err != nil {
+		return nil, fmt.Errorf("failed to decode JWK y: %w", err)
+	}
+	dBytes, err := base64.RawURLEncoding.DecodeString(jwk.D)
+	if err != nil {
+		return nil, fmt.Errorf("failed to decode JWK d: %w", err)
+	}
+
+	key := &ecdsa.PrivateKey{
+		PublicKey: ecdsa.PublicKey{
+			Curve: curve,
+			X:     new(big.Int).SetBytes(xBytes),
+			Y:     new(big.Int).SetBytes(yBytes),
+		},
+		D: new(big.Int).SetBytes(dBytes),
+	}
+
+	return key, nil
+}
+
+// aesKeyUnwrap implements AES Key Unwrap per RFC 3394.
+func aesKeyUnwrap(kek, ciphertext []byte) ([]byte, error) {
+	if len(ciphertext)%8 != 0 || len(ciphertext) < 24 {
+		return nil, fmt.Errorf("invalid ciphertext length for AES Key Unwrap: %d", len(ciphertext))
+	}
+
+	block, err := aes.NewCipher(kek)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create AES cipher: %w", err)
+	}
+
+	n := (len(ciphertext) / 8) - 1 // number of 64-bit key data blocks
+
+	// Initialize
+	a := make([]byte, 8)
+	copy(a, ciphertext[:8])
+
+	r := make([][]byte, n)
+	for i := 0; i < n; i++ {
+		r[i] = make([]byte, 8)
+		copy(r[i], ciphertext[(i+1)*8:(i+2)*8])
+	}
+
+	// Unwrap: 6 rounds
+	buf := make([]byte, 16)
+	for j := 5; j >= 0; j-- {
+		for i := n; i >= 1; i-- {
+			// A ^= (n*j + i) encoded as big-endian uint64
+			t := uint64(n*j + i)
+			tBytes := make([]byte, 8)
+			binary.BigEndian.PutUint64(tBytes, t)
+			for k := 0; k < 8; k++ {
+				a[k] ^= tBytes[k]
+			}
+
+			// B = AES-1(KEK, A || R[i])
+			copy(buf[:8], a)
+			copy(buf[8:], r[i-1])
+			block.Decrypt(buf, buf)
+
+			copy(a, buf[:8])
+			copy(r[i-1], buf[8:])
+		}
+	}
+
+	// Check the integrity check value (must be 0xA6A6A6A6A6A6A6A6)
+	defaultIV := []byte{0xA6, 0xA6, 0xA6, 0xA6, 0xA6, 0xA6, 0xA6, 0xA6}
+	for i := 0; i < 8; i++ {
+		if a[i] != defaultIV[i] {
+			return nil, fmt.Errorf("AES Key Unwrap integrity check failed")
+		}
+	}
+
+	// Concatenate unwrapped key data
+	result := make([]byte, 0, n*8)
+	for i := 0; i < n; i++ {
+		result = append(result, r[i]...)
+	}
+
+	return result, nil
+}

internal/connector/issuer/stepca/stepca.go

@@ -27,6 +27,7 @@ import (
 	"crypto/elliptic"
 	"crypto/rand"
 	"crypto/sha256"
+	"crypto/tls"
 	"crypto/x509"
 	"encoding/base64"
 	"encoding/json"
@@ -74,17 +75,37 @@ type Connector struct {
 }
 
 // New creates a new step-ca connector with the given configuration and logger.
+// If RootCertPath is set, the HTTP client will trust that CA certificate for TLS connections.
+// Otherwise, the system trust store is used (which works if setup-trust.sh has run).
 func New(config *Config, logger *slog.Logger) *Connector {
-	if config != nil && config.ValidityDays == 0 {
-		config.ValidityDays = 90
+	// Don't default ValidityDays — let step-ca use its own default duration.
+	// Operators can explicitly set ValidityDays if their step-ca is configured
+	// with longer max durations. A zero value means "omit from sign request."
+
+	httpClient := &http.Client{Timeout: 30 * time.Second}
+
+	// Load custom root CA cert if provided
+	if config != nil && config.RootCertPath != "" {
+		rootPEM, err := os.ReadFile(config.RootCertPath)
+		if err == nil {
+			pool := x509.NewCertPool()
+			if pool.AppendCertsFromPEM(rootPEM) {
+				httpClient.Transport = &http.Transport{
+					TLSClientConfig: &tls.Config{
+						RootCAs: pool,
+					},
+				}
+				logger.Info("step-ca custom root CA loaded", "path", config.RootCertPath)
+			}
+		} else {
+			logger.Warn("failed to read step-ca root cert, using system trust store", "path", config.RootCertPath, "error", err)
+		}
 	}
 
 	return &Connector{
-		config: config,
-		logger: logger,
-		httpClient: &http.Client{
-			Timeout: 30 * time.Second,
-		},
+		config:     config,
+		logger:     logger,
+		httpClient: httpClient,
 	}
 }
 
@@ -103,9 +124,7 @@ func (c *Connector) ValidateConfig(ctx context.Context, rawConfig json.RawMessag
 		return fmt.Errorf("step-ca provisioner_name is required")
 	}
 
-	if cfg.ValidityDays == 0 {
-		cfg.ValidityDays = 90
-	}
+	// Don't default ValidityDays — 0 means "let step-ca use its own default duration"
 
 	// Check CA health
 	healthURL := cfg.CAURL + "/health"
@@ -174,15 +193,18 @@ func (c *Connector) IssueCertificate(ctx context.Context, request issuer.Issuanc
 		return nil, fmt.Errorf("failed to generate provisioner token: %w", err)
 	}
 
-	// Build the sign request
-	now := time.Now()
-	notAfter := now.AddDate(0, 0, c.config.ValidityDays)
-
+	// Build the sign request.
+	// When ValidityDays is 0 (default), omit NotBefore/NotAfter so step-ca uses its
+	// own default duration (typically 24h). The signRequest struct has omitempty on
+	// both time fields, so zero-value time.Time{} gets stripped from the JSON.
 	signReq := signRequest{
-		CsrPEM:    request.CSRPEM,
-		OTT:       ott,
-		NotBefore: now,
-		NotAfter:  notAfter,
+		CsrPEM: request.CSRPEM,
+		OTT:    ott,
+	}
+	if c.config.ValidityDays > 0 {
+		now := time.Now()
+		signReq.NotBefore = now
+		signReq.NotAfter = now.AddDate(0, 0, c.config.ValidityDays)
 	}
 
 	body, err := json.Marshal(signReq)
@@ -318,39 +340,80 @@ func (c *Connector) GetOrderStatus(ctx context.Context, orderID string) (*issuer
 }
 
 // generateProvisionerToken creates a short-lived JWT (One-Time Token) for step-ca API calls.
-// This is a minimal JWT signed with the provisioner's key.
+// The JWT is signed with the provisioner's private key (loaded from the encrypted JWE file
+// at ProvisionerKeyPath and decrypted with ProvisionerPassword).
 func (c *Connector) generateProvisionerToken(subject string, sans []string) (string, error) {
-	// For the initial implementation, we generate a simple self-signed JWT.
-	// In production, the provisioner key would be loaded from the configured path.
-	// step-ca expects a JWT with: sub=<CN>, iss=<provisioner>, aud=<ca-url>/sign
+	var key *ecdsa.PrivateKey
+	var kid string
+
+	if c.config.ProvisionerKeyPath != "" {
+		// Production: load and decrypt the real provisioner key from disk
+		var err error
+		key, kid, err = c.loadProvisionerKey()
+		if err != nil {
+			return "", fmt.Errorf("failed to load provisioner key: %w", err)
+		}
+	} else {
+		// Fallback: generate an ephemeral key (for testing or when key path not configured).
+		// This won't authenticate with a real step-ca server, but allows the connector
+		// to function against mock servers in tests.
+		c.logger.Warn("no provisioner key path configured, using ephemeral key (will not work with real step-ca)")
+		var err error
+		key, err = ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+		if err != nil {
+			return "", fmt.Errorf("failed to generate ephemeral key: %w", err)
+		}
+		kid = "ephemeral"
+	}
 
 	now := time.Now()
 
+	// step-ca expects: aud = <ca-url>/1.0/sign (the sign endpoint audience)
 	claims := map[string]interface{}{
 		"sub":  subject,
 		"iss":  c.config.ProvisionerName,
-		"aud":  c.config.CAURL + "/sign",
+		"aud":  c.config.CAURL + "/1.0/sign",
 		"nbf":  now.Unix(),
 		"iat":  now.Unix(),
 		"exp":  now.Add(5 * time.Minute).Unix(),
 		"jti":  generateJTI(),
-		"sha":  c.config.ProvisionerName, // step-ca uses this for key lookup
+		"sha":  kid, // step-ca uses this to look up the provisioner by key fingerprint
 	}
 
 	if len(sans) > 0 {
 		claims["sans"] = sans
 	}
 
-	// Generate an ephemeral signing key for the token.
-	// In a full implementation, this would use the provisioner key from disk.
-	// For now, we use an ephemeral key — step-ca administrators should configure
-	// the provisioner to accept tokens from this key.
-	key, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
-	if err != nil {
-		return "", fmt.Errorf("failed to generate token signing key: %w", err)
+	return signJWTWithKID(claims, key, kid)
+}
+
+// loadProvisionerKey loads and decrypts the step-ca provisioner key from disk.
+// Returns the ECDSA private key and the key ID (JWK thumbprint).
+func (c *Connector) loadProvisionerKey() (*ecdsa.PrivateKey, string, error) {
+	if c.config.ProvisionerKeyPath == "" {
+		return nil, "", fmt.Errorf("provisioner_key_path is required for step-ca JWK authentication")
 	}
 
-	return signJWT(claims, key)
+	jweData, err := os.ReadFile(c.config.ProvisionerKeyPath)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to read provisioner key file %s: %w", c.config.ProvisionerKeyPath, err)
+	}
+
+	password := c.config.ProvisionerPassword
+	if password == "" {
+		return nil, "", fmt.Errorf("provisioner_password is required to decrypt the provisioner key")
+	}
+
+	key, kid, err := decryptProvisionerKey(jweData, password)
+	if err != nil {
+		return nil, "", fmt.Errorf("failed to decrypt provisioner key: %w", err)
+	}
+
+	c.logger.Info("provisioner key loaded and decrypted",
+		"key_path", c.config.ProvisionerKeyPath,
+		"kid", kid)
+
+	return key, kid, nil
 }
 
 // generateJTI creates a unique JWT ID.
@@ -360,14 +423,21 @@ func generateJTI() string {
 	return base64.RawURLEncoding.EncodeToString(b)
 }
 
-// signJWT creates a minimal ES256 JWT from the given claims.
-func signJWT(claims map[string]interface{}, key *ecdsa.PrivateKey) (string, error) {
-	// Header
+// signJWTWithKID creates an ES256 JWT with a key ID in the header.
+func signJWTWithKID(claims map[string]interface{}, key *ecdsa.PrivateKey, kid string) (string, error) {
+	// Header with kid so step-ca can look up the provisioner
 	header := map[string]string{
 		"alg": "ES256",
 		"typ": "JWT",
+		"kid": kid,
 	}
 
+	return signJWTRaw(claims, key, header)
+}
+
+// signJWTRaw creates an ES256 JWT from the given claims and header.
+func signJWTRaw(claims map[string]interface{}, key *ecdsa.PrivateKey, header map[string]string) (string, error) {
+
 	headerJSON, err := json.Marshal(header)
 	if err != nil {
 		return "", err

internal/connector/target/envoy/envoy.go

@@ -0,0 +1,318 @@
+package envoy
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"log/slog"
+	"os"
+	"path/filepath"
+	"strings"
+	"time"
+
+	"github.com/shankar0123/certctl/internal/connector/target"
+)
+
+// Config represents the Envoy deployment target configuration.
+// Envoy uses file-based certificate delivery — the agent writes cert/key files
+// to a directory that Envoy watches via its SDS (Secret Discovery Service)
+// file-based configuration or static filename references in the bootstrap config.
+type Config struct {
+	CertDir       string `json:"cert_dir"`        // Directory where Envoy watches for cert files (required)
+	CertFilename  string `json:"cert_filename"`   // Filename for certificate (default: cert.pem)
+	KeyFilename   string `json:"key_filename"`    // Filename for private key (default: key.pem)
+	ChainFilename string `json:"chain_filename"`  // Optional filename for chain (if set, chain written separately)
+	SDSConfig     bool   `json:"sds_config"`      // If true, write an SDS discovery JSON file for file-based SDS
+}
+
+// SDSResource represents an Envoy SDS tls_certificate resource for file-based SDS.
+// This matches Envoy's expected format for file-based Secret Discovery Service.
+type SDSResource struct {
+	Resources []SDSTLSCertificate `json:"resources"`
+}
+
+// SDSTLSCertificate represents a single SDS tls_certificate entry.
+type SDSTLSCertificate struct {
+	Type            string         `json:"@type"`
+	Name            string         `json:"name"`
+	TLSCertificate  TLSCertificate `json:"tls_certificate"`
+}
+
+// TLSCertificate contains the file paths for cert and key in Envoy's SDS format.
+type TLSCertificate struct {
+	CertificateChain DataSource `json:"certificate_chain"`
+	PrivateKey       DataSource `json:"private_key"`
+}
+
+// DataSource represents an Envoy data source pointing to a file path.
+type DataSource struct {
+	Filename string `json:"filename"`
+}
+
+// Connector implements the target.Connector interface for Envoy proxy servers.
+// This connector runs on the AGENT side and handles local certificate deployment.
+// Envoy watches the configured directory via its file-based SDS or static config
+// and automatically picks up certificate changes without an explicit reload.
+type Connector struct {
+	config *Config
+	logger *slog.Logger
+}
+
+// New creates a new Envoy target connector with the given configuration and logger.
+func New(config *Config, logger *slog.Logger) *Connector {
+	return &Connector{
+		config: config,
+		logger: logger,
+	}
+}
+
+// ValidateConfig checks that the certificate directory is configured and valid.
+func (c *Connector) ValidateConfig(ctx context.Context, rawConfig json.RawMessage) error {
+	var cfg Config
+	if err := json.Unmarshal(rawConfig, &cfg); err != nil {
+		return fmt.Errorf("invalid Envoy config: %w", err)
+	}
+
+	if cfg.CertDir == "" {
+		return fmt.Errorf("Envoy cert_dir is required")
+	}
+
+	// Default filenames if not provided
+	if cfg.CertFilename == "" {
+		cfg.CertFilename = "cert.pem"
+	}
+	if cfg.KeyFilename == "" {
+		cfg.KeyFilename = "key.pem"
+	}
+
+	// Validate filenames don't contain path separators (prevent path traversal)
+	if strings.Contains(cfg.CertFilename, "/") || strings.Contains(cfg.CertFilename, "\\") {
+		return fmt.Errorf("Envoy cert_filename must not contain path separators")
+	}
+	if strings.Contains(cfg.KeyFilename, "/") || strings.Contains(cfg.KeyFilename, "\\") {
+		return fmt.Errorf("Envoy key_filename must not contain path separators")
+	}
+	if cfg.ChainFilename != "" && (strings.Contains(cfg.ChainFilename, "/") || strings.Contains(cfg.ChainFilename, "\\")) {
+		return fmt.Errorf("Envoy chain_filename must not contain path separators")
+	}
+
+	c.logger.Info("validating Envoy configuration",
+		"cert_dir", cfg.CertDir,
+		"cert_filename", cfg.CertFilename,
+		"key_filename", cfg.KeyFilename,
+		"chain_filename", cfg.ChainFilename,
+		"sds_config", cfg.SDSConfig)
+
+	// Verify directory exists and is writable
+	if _, err := os.Stat(cfg.CertDir); os.IsNotExist(err) {
+		return fmt.Errorf("Envoy cert directory does not exist: %s", cfg.CertDir)
+	}
+
+	// Try to write a test file to verify directory is writable
+	testFile := filepath.Join(cfg.CertDir, ".certctl-write-test")
+	if err := os.WriteFile(testFile, []byte("test"), 0644); err != nil {
+		return fmt.Errorf("Envoy cert directory is not writable: %s (%w)", cfg.CertDir, err)
+	}
+	os.Remove(testFile)
+
+	c.config = &cfg
+	c.logger.Info("Envoy configuration validated")
+	return nil
+}
+
+// DeployCertificate writes the certificate and key files to the configured directory.
+// Envoy watches this directory via file-based SDS or static config references
+// and automatically picks up changes without requiring a reload command.
+//
+// Steps:
+// 1. Write certificate (+ chain if chain_filename not set) to cert_filename with mode 0644
+// 2. Write private key to key_filename with mode 0600
+// 3. If chain_filename set and chain provided, write chain separately with mode 0644
+// 4. If sds_config is true, write SDS JSON file pointing to cert/key paths
+func (c *Connector) DeployCertificate(ctx context.Context, request target.DeploymentRequest) (*target.DeploymentResult, error) {
+	c.logger.Info("deploying certificate to Envoy",
+		"cert_dir", c.config.CertDir,
+		"cert_filename", c.config.CertFilename,
+		"key_filename", c.config.KeyFilename)
+
+	startTime := time.Now()
+
+	certPath := filepath.Join(c.config.CertDir, c.config.CertFilename)
+	keyPath := filepath.Join(c.config.CertDir, c.config.KeyFilename)
+
+	// Build certificate data: if chain_filename is set, write chain separately;
+	// otherwise append chain to cert file (standard fullchain behavior)
+	certData := request.CertPEM + "\n"
+	if request.ChainPEM != "" && c.config.ChainFilename == "" {
+		certData += request.ChainPEM + "\n"
+	}
+
+	// Write certificate with mode 0644 (readable by Envoy process)
+	if err := os.WriteFile(certPath, []byte(certData), 0644); err != nil {
+		errMsg := fmt.Sprintf("failed to write certificate: %v", err)
+		c.logger.Error("certificate deployment failed", "error", err)
+		return &target.DeploymentResult{
+			Success:       false,
+			TargetAddress: certPath,
+			Message:       errMsg,
+			DeployedAt:    time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	// Write private key with secure permissions (0600: rw-------)
+	if request.KeyPEM != "" {
+		if err := os.WriteFile(keyPath, []byte(request.KeyPEM), 0600); err != nil {
+			errMsg := fmt.Sprintf("failed to write private key: %v", err)
+			c.logger.Error("key deployment failed", "error", err)
+			return &target.DeploymentResult{
+				Success:       false,
+				TargetAddress: keyPath,
+				Message:       errMsg,
+				DeployedAt:    time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+	}
+
+	// Write chain separately if chain_filename is configured
+	if c.config.ChainFilename != "" && request.ChainPEM != "" {
+		chainPath := filepath.Join(c.config.CertDir, c.config.ChainFilename)
+		if err := os.WriteFile(chainPath, []byte(request.ChainPEM+"\n"), 0644); err != nil {
+			errMsg := fmt.Sprintf("failed to write chain: %v", err)
+			c.logger.Error("chain deployment failed", "error", err)
+			return &target.DeploymentResult{
+				Success:       false,
+				TargetAddress: chainPath,
+				Message:       errMsg,
+				DeployedAt:    time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+	}
+
+	// Write SDS JSON file if configured
+	if c.config.SDSConfig {
+		if err := c.writeSDSConfig(); err != nil {
+			errMsg := fmt.Sprintf("failed to write SDS config: %v", err)
+			c.logger.Error("SDS config deployment failed", "error", err)
+			return &target.DeploymentResult{
+				Success:       false,
+				TargetAddress: certPath,
+				Message:       errMsg,
+				DeployedAt:    time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+	}
+
+	deploymentDuration := time.Since(startTime)
+	c.logger.Info("certificate deployed to Envoy successfully",
+		"duration", deploymentDuration.String(),
+		"cert_path", certPath,
+		"key_path", keyPath,
+		"sds_config", c.config.SDSConfig)
+
+	metadata := map[string]string{
+		"cert_path":   certPath,
+		"key_path":    keyPath,
+		"duration_ms": fmt.Sprintf("%d", deploymentDuration.Milliseconds()),
+	}
+	if c.config.SDSConfig {
+		metadata["sds_config_path"] = filepath.Join(c.config.CertDir, "sds.json")
+	}
+
+	return &target.DeploymentResult{
+		Success:       true,
+		TargetAddress: certPath,
+		DeploymentID:  fmt.Sprintf("envoy-%d", time.Now().Unix()),
+		Message:       "Certificate deployed to Envoy (file-based SDS will auto-reload)",
+		DeployedAt:    time.Now(),
+		Metadata:      metadata,
+	}, nil
+}
+
+// writeSDSConfig writes an Envoy SDS JSON file that references the cert/key file paths.
+// This file is consumed by Envoy's file-based SDS provider (path_config_source).
+func (c *Connector) writeSDSConfig() error {
+	certPath := filepath.Join(c.config.CertDir, c.config.CertFilename)
+	keyPath := filepath.Join(c.config.CertDir, c.config.KeyFilename)
+
+	sdsResource := SDSResource{
+		Resources: []SDSTLSCertificate{
+			{
+				Type: "type.googleapis.com/envoy.extensions.transport_sockets.tls.v3.Secret",
+				Name: "server_cert",
+				TLSCertificate: TLSCertificate{
+					CertificateChain: DataSource{Filename: certPath},
+					PrivateKey:       DataSource{Filename: keyPath},
+				},
+			},
+		},
+	}
+
+	sdsJSON, err := json.MarshalIndent(sdsResource, "", "  ")
+	if err != nil {
+		return fmt.Errorf("failed to marshal SDS config: %w", err)
+	}
+
+	sdsPath := filepath.Join(c.config.CertDir, "sds.json")
+	if err := os.WriteFile(sdsPath, sdsJSON, 0644); err != nil {
+		return fmt.Errorf("failed to write SDS config file: %w", err)
+	}
+
+	c.logger.Info("SDS config file written", "path", sdsPath)
+	return nil
+}
+
+// ValidateDeployment verifies that the deployed certificate files are readable.
+// It checks that both the certificate and key files exist and are accessible.
+func (c *Connector) ValidateDeployment(ctx context.Context, request target.ValidationRequest) (*target.ValidationResult, error) {
+	c.logger.Info("validating Envoy deployment",
+		"certificate_id", request.CertificateID,
+		"serial", request.Serial)
+
+	startTime := time.Now()
+
+	certPath := filepath.Join(c.config.CertDir, c.config.CertFilename)
+	keyPath := filepath.Join(c.config.CertDir, c.config.KeyFilename)
+
+	// Verify certificate file exists and is readable
+	if _, err := os.Stat(certPath); os.IsNotExist(err) {
+		errMsg := fmt.Sprintf("certificate file not found: %s", certPath)
+		c.logger.Error("validation failed", "error", err)
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: certPath,
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	// Verify key file exists and is readable
+	if _, err := os.Stat(keyPath); os.IsNotExist(err) {
+		errMsg := fmt.Sprintf("private key file not found: %s", keyPath)
+		c.logger.Error("validation failed", "error", err)
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: keyPath,
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	validationDuration := time.Since(startTime)
+	c.logger.Info("Envoy deployment validated successfully",
+		"duration", validationDuration.String())
+
+	return &target.ValidationResult{
+		Valid:         true,
+		Serial:        request.Serial,
+		TargetAddress: certPath,
+		Message:       "Certificate and key files accessible",
+		ValidatedAt:   time.Now(),
+		Metadata: map[string]string{
+			"cert_path":   certPath,
+			"key_path":    keyPath,
+			"duration_ms": fmt.Sprintf("%d", validationDuration.Milliseconds()),
+		},
+	}, nil
+}

internal/connector/target/envoy/envoy_test.go

@@ -0,0 +1,394 @@
+package envoy_test
+
+import (
+	"context"
+	"encoding/json"
+	"log/slog"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"github.com/shankar0123/certctl/internal/connector/target"
+	"github.com/shankar0123/certctl/internal/connector/target/envoy"
+)
+
+func testLogger() *slog.Logger {
+	return slog.New(slog.NewTextHandler(os.Stdout, &slog.HandlerOptions{Level: slog.LevelDebug}))
+}
+
+func TestEnvoyConnector_ValidateConfig_Success(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{
+		CertDir:      tmpDir,
+		CertFilename: "cert.pem",
+		KeyFilename:  "key.pem",
+	}
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err != nil {
+		t.Fatalf("ValidateConfig failed: %v", err)
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_InvalidJSON(t *testing.T) {
+	ctx := context.Background()
+	connector := envoy.New(&envoy.Config{}, testLogger())
+	if err := connector.ValidateConfig(ctx, json.RawMessage(`{invalid}`)); err == nil {
+		t.Fatal("expected error for invalid JSON")
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_MissingCertDir(t *testing.T) {
+	ctx := context.Background()
+	cfg := envoy.Config{CertFilename: "cert.pem", KeyFilename: "key.pem"}
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err == nil {
+		t.Fatal("expected error for missing cert_dir")
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_DirectoryNotExists(t *testing.T) {
+	ctx := context.Background()
+	cfg := envoy.Config{CertDir: "/nonexistent/directory"}
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err == nil {
+		t.Fatal("expected error for non-existent directory")
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_PathTraversal_CertFilename(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+	cfg := envoy.Config{CertDir: tmpDir, CertFilename: "../../../etc/passwd"}
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err == nil {
+		t.Fatal("expected error for path traversal in cert_filename")
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_PathTraversal_KeyFilename(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+	cfg := envoy.Config{CertDir: tmpDir, KeyFilename: "sub/key.pem"}
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err == nil {
+		t.Fatal("expected error for path traversal in key_filename")
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_PathTraversal_ChainFilename(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+	cfg := envoy.Config{CertDir: tmpDir, ChainFilename: "../chain.pem"}
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err == nil {
+		t.Fatal("expected error for path traversal in chain_filename")
+	}
+}
+
+func TestEnvoyConnector_ValidateConfig_DefaultFilenames(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+	cfg := envoy.Config{CertDir: tmpDir} // No filenames — should use defaults
+
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	if err := connector.ValidateConfig(ctx, rawConfig); err != nil {
+		t.Fatalf("ValidateConfig with defaults failed: %v", err)
+	}
+}
+
+func TestEnvoyConnector_DeployCertificate_Success(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{CertDir: tmpDir, CertFilename: "cert.pem", KeyFilename: "key.pem"}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	request := target.DeploymentRequest{
+		CertPEM:  "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----",
+		KeyPEM:   "-----BEGIN PRIVATE KEY-----\nMIIE...\n-----END PRIVATE KEY-----",
+		ChainPEM: "-----BEGIN CERTIFICATE-----\nCAcert...\n-----END CERTIFICATE-----",
+	}
+
+	result, err := connector.DeployCertificate(ctx, request)
+	if err != nil {
+		t.Fatalf("DeployCertificate failed: %v", err)
+	}
+	if !result.Success {
+		t.Fatalf("deployment should succeed, got: %s", result.Message)
+	}
+
+	// Verify cert file was created with chain appended (no chain_filename set)
+	certData, err := os.ReadFile(filepath.Join(tmpDir, "cert.pem"))
+	if err != nil {
+		t.Fatalf("failed to read cert file: %v", err)
+	}
+	if got := string(certData); got != "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----\n-----BEGIN CERTIFICATE-----\nCAcert...\n-----END CERTIFICATE-----\n" {
+		t.Fatalf("cert content mismatch: got %q", got)
+	}
+
+	// Verify key file created with correct permissions
+	keyPath := filepath.Join(tmpDir, "key.pem")
+	keyInfo, err := os.Stat(keyPath)
+	if err != nil {
+		t.Fatalf("key file not found: %v", err)
+	}
+	if perms := keyInfo.Mode().Perm(); perms != 0600 {
+		t.Fatalf("key permissions are %o, expected 0600", perms)
+	}
+}
+
+func TestEnvoyConnector_DeployCertificate_WithoutChain(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{CertDir: tmpDir, CertFilename: "cert.pem", KeyFilename: "key.pem"}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	request := target.DeploymentRequest{
+		CertPEM: "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----",
+		KeyPEM:  "-----BEGIN PRIVATE KEY-----\nMIIE...\n-----END PRIVATE KEY-----",
+	}
+
+	result, err := connector.DeployCertificate(ctx, request)
+	if err != nil {
+		t.Fatalf("DeployCertificate failed: %v", err)
+	}
+	if !result.Success {
+		t.Fatalf("deployment should succeed, got: %s", result.Message)
+	}
+
+	// Cert file should only contain the leaf cert (no chain)
+	certData, _ := os.ReadFile(filepath.Join(tmpDir, "cert.pem"))
+	if got := string(certData); got != "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----\n" {
+		t.Fatalf("cert content mismatch: got %q", got)
+	}
+}
+
+func TestEnvoyConnector_DeployCertificate_SeparateChainFile(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{
+		CertDir:       tmpDir,
+		CertFilename:  "cert.pem",
+		KeyFilename:   "key.pem",
+		ChainFilename: "chain.pem",
+	}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	request := target.DeploymentRequest{
+		CertPEM:  "-----BEGIN CERTIFICATE-----\nleaf...\n-----END CERTIFICATE-----",
+		KeyPEM:   "-----BEGIN PRIVATE KEY-----\nMIIE...\n-----END PRIVATE KEY-----",
+		ChainPEM: "-----BEGIN CERTIFICATE-----\nCA...\n-----END CERTIFICATE-----",
+	}
+
+	result, err := connector.DeployCertificate(ctx, request)
+	if err != nil {
+		t.Fatalf("DeployCertificate failed: %v", err)
+	}
+	if !result.Success {
+		t.Fatalf("deployment should succeed, got: %s", result.Message)
+	}
+
+	// Cert file should only contain leaf (chain is separate)
+	certData, _ := os.ReadFile(filepath.Join(tmpDir, "cert.pem"))
+	if got := string(certData); got != "-----BEGIN CERTIFICATE-----\nleaf...\n-----END CERTIFICATE-----\n" {
+		t.Fatalf("cert should not contain chain when chain_filename is set: got %q", got)
+	}
+
+	// Chain file should exist with chain data
+	chainData, err := os.ReadFile(filepath.Join(tmpDir, "chain.pem"))
+	if err != nil {
+		t.Fatalf("chain file not found: %v", err)
+	}
+	if got := string(chainData); got != "-----BEGIN CERTIFICATE-----\nCA...\n-----END CERTIFICATE-----\n" {
+		t.Fatalf("chain content mismatch: got %q", got)
+	}
+}
+
+func TestEnvoyConnector_DeployCertificate_WithSDSConfig(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{
+		CertDir:      tmpDir,
+		CertFilename: "cert.pem",
+		KeyFilename:  "key.pem",
+		SDSConfig:    true,
+	}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	request := target.DeploymentRequest{
+		CertPEM: "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----",
+		KeyPEM:  "-----BEGIN PRIVATE KEY-----\nMIIE...\n-----END PRIVATE KEY-----",
+	}
+
+	result, err := connector.DeployCertificate(ctx, request)
+	if err != nil {
+		t.Fatalf("DeployCertificate failed: %v", err)
+	}
+	if !result.Success {
+		t.Fatalf("deployment should succeed, got: %s", result.Message)
+	}
+
+	// Verify SDS JSON file was created
+	sdsPath := filepath.Join(tmpDir, "sds.json")
+	sdsData, err := os.ReadFile(sdsPath)
+	if err != nil {
+		t.Fatalf("SDS config file not found: %v", err)
+	}
+
+	// Parse and verify SDS JSON structure
+	var sdsResource envoy.SDSResource
+	if err := json.Unmarshal(sdsData, &sdsResource); err != nil {
+		t.Fatalf("invalid SDS JSON: %v", err)
+	}
+
+	if len(sdsResource.Resources) != 1 {
+		t.Fatalf("expected 1 SDS resource, got %d", len(sdsResource.Resources))
+	}
+
+	res := sdsResource.Resources[0]
+	if res.Type != "type.googleapis.com/envoy.extensions.transport_sockets.tls.v3.Secret" {
+		t.Fatalf("wrong @type: %s", res.Type)
+	}
+	if res.Name != "server_cert" {
+		t.Fatalf("wrong name: %s", res.Name)
+	}
+
+	expectedCertPath := filepath.Join(tmpDir, "cert.pem")
+	expectedKeyPath := filepath.Join(tmpDir, "key.pem")
+	if res.TLSCertificate.CertificateChain.Filename != expectedCertPath {
+		t.Fatalf("cert chain path mismatch: got %s, want %s", res.TLSCertificate.CertificateChain.Filename, expectedCertPath)
+	}
+	if res.TLSCertificate.PrivateKey.Filename != expectedKeyPath {
+		t.Fatalf("private key path mismatch: got %s, want %s", res.TLSCertificate.PrivateKey.Filename, expectedKeyPath)
+	}
+
+	// Verify SDS path is in metadata
+	if result.Metadata["sds_config_path"] != sdsPath {
+		t.Fatalf("SDS config path not in metadata")
+	}
+}
+
+func TestEnvoyConnector_DeployCertificate_WriteError(t *testing.T) {
+	ctx := context.Background()
+
+	cfg := envoy.Config{
+		CertDir:      "/root/envoy/certs",
+		CertFilename: "cert.pem",
+		KeyFilename:  "key.pem",
+	}
+	connector := envoy.New(&cfg, testLogger())
+
+	request := target.DeploymentRequest{
+		CertPEM: "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----",
+		KeyPEM:  "-----BEGIN PRIVATE KEY-----\nMIIE...\n-----END PRIVATE KEY-----",
+	}
+
+	result, err := connector.DeployCertificate(ctx, request)
+	if err == nil {
+		t.Fatal("expected error for write failure")
+	}
+	if result.Success {
+		t.Fatal("deployment should fail")
+	}
+}
+
+func TestEnvoyConnector_ValidateDeployment_Success(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{CertDir: tmpDir, CertFilename: "cert.pem", KeyFilename: "key.pem"}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	// First deploy
+	deployReq := target.DeploymentRequest{
+		CertPEM: "-----BEGIN CERTIFICATE-----\nMIIC...\n-----END CERTIFICATE-----",
+		KeyPEM:  "-----BEGIN PRIVATE KEY-----\nMIIE...\n-----END PRIVATE KEY-----",
+	}
+	connector.DeployCertificate(ctx, deployReq)
+
+	// Then validate
+	validateReq := target.ValidationRequest{
+		CertificateID: "mc-test",
+		Serial:        "123456",
+	}
+
+	result, err := connector.ValidateDeployment(ctx, validateReq)
+	if err != nil {
+		t.Fatalf("ValidateDeployment failed: %v", err)
+	}
+	if !result.Valid {
+		t.Fatalf("validation should succeed, got: %s", result.Message)
+	}
+	if result.Serial != "123456" {
+		t.Fatalf("serial mismatch: expected 123456, got %s", result.Serial)
+	}
+}
+
+func TestEnvoyConnector_ValidateDeployment_CertFileNotFound(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{CertDir: tmpDir, CertFilename: "cert.pem", KeyFilename: "key.pem"}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	validateReq := target.ValidationRequest{CertificateID: "mc-test", Serial: "123456"}
+	result, err := connector.ValidateDeployment(ctx, validateReq)
+	if err == nil {
+		t.Fatal("expected error for missing certificate file")
+	}
+	if result.Valid {
+		t.Fatal("validation should fail")
+	}
+}
+
+func TestEnvoyConnector_ValidateDeployment_KeyFileNotFound(t *testing.T) {
+	ctx := context.Background()
+	tmpDir := t.TempDir()
+
+	cfg := envoy.Config{CertDir: tmpDir, CertFilename: "cert.pem", KeyFilename: "key.pem"}
+	connector := envoy.New(&cfg, testLogger())
+	rawConfig, _ := json.Marshal(cfg)
+	_ = connector.ValidateConfig(ctx, rawConfig)
+
+	// Write cert but not key
+	os.WriteFile(filepath.Join(tmpDir, "cert.pem"), []byte("cert"), 0644)
+
+	validateReq := target.ValidationRequest{CertificateID: "mc-test", Serial: "123456"}
+	result, err := connector.ValidateDeployment(ctx, validateReq)
+	if err == nil {
+		t.Fatal("expected error for missing key file")
+	}
+	if result.Valid {
+		t.Fatal("validation should fail")
+	}
+}

internal/connector/target/iis/iis.go

@@ -2,101 +2,241 @@ package iis
 
 import (
 	"context"
+	"crypto/rand"
+	"crypto/sha1"
+	"crypto/x509"
+	"encoding/base64"
+	"encoding/hex"
 	"encoding/json"
+	"encoding/pem"
 	"fmt"
 	"log/slog"
-	"runtime"
+	"os"
+	"os/exec"
+	"regexp"
+	"strings"
 	"time"
 
 	"github.com/shankar0123/certctl/internal/connector/target"
+	pkcs12 "software.sslmate.com/src/go-pkcs12"
 )
 
 // Config represents the IIS deployment target configuration.
-// This configuration is for Windows agents that manage IIS servers.
+// Supports two modes:
+//   - "local" (default): runs PowerShell locally on a Windows agent
+//   - "winrm": connects to a remote Windows server via WinRM (proxy agent pattern)
 type Config struct {
 	Hostname    string `json:"hostname"`     // Target hostname or IP
 	SiteName    string `json:"site_name"`    // IIS site name (e.g., "Default Web Site")
 	CertStore   string `json:"cert_store"`   // Windows cert store (e.g., "My", "WebHosting")
 	BindingInfo string `json:"binding_info"` // Binding info (e.g., "*.example.com")
+	Port        int    `json:"port"`         // HTTPS port (default 443)
+	SNI         bool   `json:"sni"`          // Enable Server Name Indication
+	IPAddress   string `json:"ip_address"`   // Bind to specific IP (default "*")
+	Mode        string `json:"mode"`         // "local" (default) or "winrm"
+
+	// WinRM settings (only used when Mode is "winrm")
+	WinRM WinRMConfig `json:"winrm"`
+}
+
+// PowerShellExecutor abstracts PowerShell command execution for testability.
+// On real Windows deployments, the realExecutor calls powershell.exe directly.
+// Tests inject a mock executor to verify command construction without Windows.
+type PowerShellExecutor interface {
+	Execute(ctx context.Context, script string) (string, error)
+}
+
+// realExecutor calls powershell.exe on the local system.
+type realExecutor struct{}
+
+func (e *realExecutor) Execute(ctx context.Context, script string) (string, error) {
+	cmd := exec.CommandContext(ctx, "powershell.exe", "-NoProfile", "-NonInteractive", "-Command", script)
+	output, err := cmd.CombinedOutput()
+	return string(output), err
 }
 
 // Connector implements the target.Connector interface for IIS (Internet Information Services).
-// This connector runs on Windows agents and manages certificate deployment via IIS.
+// This connector runs on Windows agents and manages certificate deployment via PowerShell.
 //
 // IIS certificate management requires:
-// - Windows Server with IIS installed
-// - PowerShell execution available
-// - Administrative privileges
+//   - Windows Server with IIS installed
+//   - PowerShell execution available
+//   - Administrative privileges
 //
-// TODO: Implement actual PowerShell command execution for:
-// - Certificate import: Import-PfxCertificate
-// - IIS binding update: New-WebBinding, Set-WebBinding
-// - Validation: Get-WebBinding
+// Deployment flow:
+//  1. Convert PEM cert+key to PFX (PKCS#12) format via go-pkcs12
+//  2. Import PFX to Windows certificate store via Import-PfxCertificate
+//  3. Compute SHA-1 thumbprint (IIS certificate identifier)
+//  4. Update IIS HTTPS binding via New-WebBinding + AddSslCertificate
+//  5. Verify binding is active via Get-WebBinding
 type Connector struct {
-	config *Config
-	logger *slog.Logger
+	config   *Config
+	logger   *slog.Logger
+	executor PowerShellExecutor
 }
 
 // New creates a new IIS target connector with the given configuration and logger.
-func New(config *Config, logger *slog.Logger) *Connector {
+// In "local" mode (default), uses the real PowerShell executor.
+// In "winrm" mode, creates a WinRM client for remote execution.
+func New(config *Config, logger *slog.Logger) (*Connector, error) {
+	mode := config.Mode
+	if mode == "" {
+		mode = "local"
+	}
+
+	var executor PowerShellExecutor
+	switch mode {
+	case "local":
+		executor = &realExecutor{}
+	case "winrm":
+		winrmExec, err := newWinRMExecutor(&config.WinRM)
+		if err != nil {
+			return nil, fmt.Errorf("failed to initialize WinRM executor: %w", err)
+		}
+		executor = winrmExec
+	default:
+		return nil, fmt.Errorf("unsupported IIS connector mode %q (must be 'local' or 'winrm')", mode)
+	}
+
 	return &Connector{
-		config: config,
-		logger: logger,
+		config:   config,
+		logger:   logger,
+		executor: executor,
+	}, nil
+}
+
+// NewWithExecutor creates a new IIS target connector with an injected executor.
+// Used in tests to mock PowerShell execution on non-Windows platforms.
+func NewWithExecutor(config *Config, logger *slog.Logger, executor PowerShellExecutor) *Connector {
+	return &Connector{
+		config:   config,
+		logger:   logger,
+		executor: executor,
 	}
 }
 
+// validIISName matches safe IIS site names and cert store names.
+// Allows alphanumeric, spaces, underscores, hyphens, and dots.
+var validIISName = regexp.MustCompile(`^[a-zA-Z0-9 _\-\.]+$`)
+
+// validateIISName checks that an IIS name field contains only safe characters.
+// This prevents PowerShell injection via malicious site or store names.
+func validateIISName(name, field string) error {
+	if name == "" {
+		return fmt.Errorf("%s is required", field)
+	}
+	if len(name) > 256 {
+		return fmt.Errorf("%s exceeds maximum length (256 characters)", field)
+	}
+	if !validIISName.MatchString(name) {
+		return fmt.Errorf("%s contains invalid characters (allowed: alphanumeric, space, underscore, hyphen, dot)", field)
+	}
+	return nil
+}
+
+// validIPOrWildcard matches valid IP addresses or the wildcard "*".
+var validIPOrWildcard = regexp.MustCompile(`^(\*|(\d{1,3}\.){3}\d{1,3})$`)
+
 // ValidateConfig checks that the IIS configuration is valid and accessible.
-// It verifies that we're on Windows and that the IIS site exists.
-//
-// TODO: Implement actual PowerShell checks.
+// It verifies field values, PowerShell availability, and optionally checks that
+// the IIS site exists and the cert store is accessible.
 func (c *Connector) ValidateConfig(ctx context.Context, rawConfig json.RawMessage) error {
 	var cfg Config
 	if err := json.Unmarshal(rawConfig, &cfg); err != nil {
 		return fmt.Errorf("invalid IIS config: %w", err)
 	}
 
-	if cfg.SiteName == "" || cfg.CertStore == "" {
-		return fmt.Errorf("IIS site_name and cert_store are required")
+	// Validate required fields
+	if err := validateIISName(cfg.SiteName, "site_name"); err != nil {
+		return err
+	}
+	if err := validateIISName(cfg.CertStore, "cert_store"); err != nil {
+		return err
 	}
 
-	// Verify we're on Windows
-	if runtime.GOOS != "windows" {
-		return fmt.Errorf("IIS connector only runs on Windows, got %s", runtime.GOOS)
+	// Apply defaults
+	if cfg.Port == 0 {
+		cfg.Port = 443
+	}
+	if cfg.IPAddress == "" {
+		cfg.IPAddress = "*"
+	}
+
+	// Validate port range
+	if cfg.Port < 1 || cfg.Port > 65535 {
+		return fmt.Errorf("port must be between 1 and 65535, got %d", cfg.Port)
+	}
+
+	// Validate IP address format
+	if !validIPOrWildcard.MatchString(cfg.IPAddress) {
+		return fmt.Errorf("ip_address must be a valid IPv4 address or '*', got %q", cfg.IPAddress)
+	}
+
+	// Validate binding_info if provided (safe characters only)
+	if cfg.BindingInfo != "" {
+		if len(cfg.BindingInfo) > 512 {
+			return fmt.Errorf("binding_info exceeds maximum length (512 characters)")
+		}
+		// Allow typical binding chars: alphanumeric, *, :, ., -
+		validBinding := regexp.MustCompile(`^[a-zA-Z0-9\*\:\.\-]+$`)
+		if !validBinding.MatchString(cfg.BindingInfo) {
+			return fmt.Errorf("binding_info contains invalid characters")
+		}
+	}
+
+	// Apply mode default
+	if cfg.Mode == "" {
+		cfg.Mode = "local"
+	}
+	if cfg.Mode != "local" && cfg.Mode != "winrm" {
+		return fmt.Errorf("unsupported mode %q (must be 'local' or 'winrm')", cfg.Mode)
 	}
 
 	c.logger.Info("validating IIS configuration",
 		"site_name", cfg.SiteName,
 		"cert_store", cfg.CertStore,
-		"hostname", cfg.Hostname)
+		"hostname", cfg.Hostname,
+		"port", cfg.Port,
+		"mode", cfg.Mode)
 
-	// TODO: Implement PowerShell check
-	// In production:
-	//   1. Run PowerShell command: Get-IISSite -Name {SiteName}
-	//   2. Verify site exists and is running
-	//   3. Check cert store: Get-Item -Path "Cert:\LocalMachine\{CertStore}"
+	// Verify PowerShell is available (only in local mode — WinRM handles this remotely)
+	if cfg.Mode == "local" {
+		if _, err := exec.LookPath("powershell.exe"); err != nil {
+			return fmt.Errorf("powershell.exe not found in PATH: %w", err)
+		}
+	}
 
-	c.logger.Warn("IIS validation not yet fully implemented",
-		"site_name", cfg.SiteName)
+	// Verify IIS site exists
+	siteCheckScript := fmt.Sprintf(`Get-Website -Name '%s' | Select-Object -ExpandProperty Name`, cfg.SiteName)
+	output, err := c.executor.Execute(ctx, siteCheckScript)
+	if err != nil {
+		return fmt.Errorf("IIS site %q not found or inaccessible: %s (error: %w)", cfg.SiteName, strings.TrimSpace(output), err)
+	}
+
+	// Verify cert store is accessible
+	storeCheckScript := fmt.Sprintf(`Test-Path 'Cert:\LocalMachine\%s'`, cfg.CertStore)
+	output, err = c.executor.Execute(ctx, storeCheckScript)
+	if err != nil || !strings.Contains(strings.TrimSpace(output), "True") {
+		return fmt.Errorf("certificate store %q is not accessible: %s", cfg.CertStore, strings.TrimSpace(output))
+	}
 
 	c.config = &cfg
+	c.logger.Info("IIS configuration validated",
+		"site_name", cfg.SiteName,
+		"cert_store", cfg.CertStore)
 	return nil
 }
 
 // DeployCertificate imports a certificate to the Windows certificate store and updates
 // the IIS binding to use the new certificate.
 //
-// The IIS deployment process (via PowerShell):
-//  1. Create a temporary PFX file from the certificate and existing private key
-//     (Note: The private key is managed by the agent, not provided by the control plane)
-//  2. Import the PFX to the Windows certificate store (My store by default)
-//  3. Get the certificate thumbprint
-//  4. Update the IIS binding to use the new certificate by thumbprint
-//  5. Verify the binding is active
-//
-// TODO: Implement actual PowerShell commands:
-// - Import-PfxCertificate -FilePath {pfxPath} -CertStoreLocation "Cert:\LocalMachine\My"
-// - Get-ChildItem -Path "Cert:\LocalMachine\My" | Where {$_.Subject -eq "CN=..."}
-// - Set-WebBinding -Name {SiteName} -BindingInformation "{BindingInfo}" -Protocol https -SslFlags 1 -CertificateThumbprint {thumbprint}
+// Deployment flow:
+//  1. Convert PEM cert+key+chain to PFX format (go-pkcs12 with random password)
+//  2. Write PFX to temp file (cleaned up on exit, even on error)
+//  3. Compute SHA-1 thumbprint from DER cert (matches Windows certutil output)
+//  4. Import PFX to Windows cert store via Import-PfxCertificate
+//  5. Update IIS HTTPS binding via New-WebBinding + AddSslCertificate
+//  6. Return result with thumbprint in metadata
 func (c *Connector) DeployCertificate(ctx context.Context, request target.DeploymentRequest) (*target.DeploymentResult, error) {
 	c.logger.Info("deploying certificate to IIS",
 		"site_name", c.config.SiteName,
@@ -104,44 +244,204 @@ func (c *Connector) DeployCertificate(ctx context.Context, request target.Deploy
 
 	startTime := time.Now()
 
-	// TODO: Implement IIS certificate deployment
-	// In production:
-	//   1. Create temporary PFX from CertPEM and ChainPEM
-	//      (Private key should already exist on the agent)
-	//   2. Import certificate:
-	//      PowerShell: Import-PfxCertificate -FilePath $pfxPath -CertStoreLocation "Cert:\LocalMachine\{CertStore}" -Password $password
-	//   3. Get certificate thumbprint:
-	//      PowerShell: (Get-ChildItem -Path "Cert:\LocalMachine\{CertStore}" | Where {$_.Subject -like "*CN=*"}).Thumbprint
-	//   4. Update IIS binding:
-	//      PowerShell: Set-WebBinding -Name "{SiteName}" -BindingInformation "{BindingInfo}:443:*.example.com" -Protocol https -CertificateThumbprint $thumbprint
-	//   5. Remove temporary PFX file
+	// Validate we have a private key (required for PFX creation)
+	if request.KeyPEM == "" {
+		errMsg := "private key (KeyPEM) is required for IIS deployment"
+		c.logger.Error("deployment failed", "error", errMsg)
+		return &target.DeploymentResult{
+			Success:    false,
+			Message:    errMsg,
+			DeployedAt: time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	// Step 1: Create PFX from PEM inputs
+	pfxPassword, err := generateRandomPassword(32)
+	if err != nil {
+		errMsg := fmt.Sprintf("failed to generate PFX password: %v", err)
+		c.logger.Error("deployment failed", "error", err)
+		return &target.DeploymentResult{
+			Success:    false,
+			Message:    errMsg,
+			DeployedAt: time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	pfxData, err := createPFX(request.CertPEM, request.KeyPEM, request.ChainPEM, pfxPassword)
+	if err != nil {
+		errMsg := fmt.Sprintf("failed to create PFX: %v", err)
+		c.logger.Error("PFX creation failed", "error", err)
+		return &target.DeploymentResult{
+			Success:    false,
+			Message:    errMsg,
+			DeployedAt: time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	// Step 2+3: Compute thumbprint and import PFX
+	// In local mode: write PFX to temp file, import via file path
+	// In WinRM mode: base64-encode PFX, decode on remote side to temp file, import, clean up
+	thumbprint, err := computeThumbprint(request.CertPEM)
+	if err != nil {
+		errMsg := fmt.Sprintf("failed to compute certificate thumbprint: %v", err)
+		c.logger.Error("deployment failed", "error", err)
+		return &target.DeploymentResult{
+			Success:    false,
+			Message:    errMsg,
+			DeployedAt: time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	c.logger.Debug("certificate thumbprint computed", "thumbprint", thumbprint)
+
+	// Step 4: Import PFX to Windows certificate store
+	var importScript string
+	mode := c.config.Mode
+	if mode == "" {
+		mode = "local"
+	}
+
+	if mode == "winrm" {
+		// WinRM mode: base64-encode PFX, decode on remote, import, cleanup
+		pfxBase64 := base64.StdEncoding.EncodeToString(pfxData)
+		importScript = fmt.Sprintf(
+			`$pfxPath = [System.IO.Path]::GetTempFileName() + '.pfx'; `+
+				`[System.IO.File]::WriteAllBytes($pfxPath, [System.Convert]::FromBase64String('%s')); `+
+				`try { `+
+				`$password = ConvertTo-SecureString -String '%s' -AsPlainText -Force; `+
+				`Import-PfxCertificate -FilePath $pfxPath -CertStoreLocation 'Cert:\LocalMachine\%s' -Password $password `+
+				`} finally { Remove-Item -Path $pfxPath -Force -ErrorAction SilentlyContinue }`,
+			pfxBase64, pfxPassword, c.config.CertStore,
+		)
+	} else {
+		// Local mode: write PFX to local temp file
+		tmpFile, fileErr := os.CreateTemp("", "certctl-*.pfx")
+		if fileErr != nil {
+			errMsg := fmt.Sprintf("failed to create temp PFX file: %v", fileErr)
+			c.logger.Error("deployment failed", "error", fileErr)
+			return &target.DeploymentResult{
+				Success:    false,
+				Message:    errMsg,
+				DeployedAt: time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+		pfxPath := tmpFile.Name()
+		defer os.Remove(pfxPath) // Always clean up temp PFX
+
+		if _, writeErr := tmpFile.Write(pfxData); writeErr != nil {
+			tmpFile.Close()
+			errMsg := fmt.Sprintf("failed to write temp PFX file: %v", writeErr)
+			c.logger.Error("deployment failed", "error", writeErr)
+			return &target.DeploymentResult{
+				Success:    false,
+				Message:    errMsg,
+				DeployedAt: time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+		tmpFile.Close()
+
+		importScript = fmt.Sprintf(
+			`$password = ConvertTo-SecureString -String '%s' -AsPlainText -Force; `+
+				`Import-PfxCertificate -FilePath '%s' -CertStoreLocation 'Cert:\LocalMachine\%s' -Password $password`,
+			pfxPassword, pfxPath, c.config.CertStore,
+		)
+	}
+
+	output, err := c.executor.Execute(ctx, importScript)
+	if err != nil {
+		errMsg := fmt.Sprintf("PFX import failed: %v (output: %s)", err, strings.TrimSpace(output))
+		c.logger.Error("PFX import failed",
+			"error", err,
+			"output", strings.TrimSpace(output),
+			"cert_store", c.config.CertStore)
+		return &target.DeploymentResult{
+			Success:       false,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			DeployedAt:    time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	c.logger.Info("PFX imported to certificate store",
+		"cert_store", c.config.CertStore,
+		"thumbprint", thumbprint)
+
+	// Step 5: Update IIS HTTPS binding
+	port := c.config.Port
+	if port == 0 {
+		port = 443
+	}
+	ipAddress := c.config.IPAddress
+	if ipAddress == "" {
+		ipAddress = "*"
+	}
+	hostHeader := c.config.BindingInfo
+	sniFlag := 0
+	if c.config.SNI {
+		sniFlag = 1
+	}
+
+	bindingScript := fmt.Sprintf(
+		// Remove existing HTTPS binding on this port (if any), then create new one
+		`$existing = Get-WebBinding -Name '%s' -Protocol 'https' -Port %d -ErrorAction SilentlyContinue; `+
+			`if ($existing) { $existing | Remove-WebBinding }; `+
+			`New-WebBinding -Name '%s' -Protocol 'https' -Port %d -IPAddress '%s' -HostHeader '%s' -SslFlags %d; `+
+			`$binding = Get-WebBinding -Name '%s' -Protocol 'https' -Port %d; `+
+			`$binding.AddSslCertificate('%s', '%s')`,
+		c.config.SiteName, port,
+		c.config.SiteName, port, ipAddress, hostHeader, sniFlag,
+		c.config.SiteName, port,
+		thumbprint, c.config.CertStore,
+	)
+
+	output, err = c.executor.Execute(ctx, bindingScript)
+	if err != nil {
+		errMsg := fmt.Sprintf("IIS binding update failed: %v (output: %s)", err, strings.TrimSpace(output))
+		c.logger.Error("IIS binding update failed",
+			"error", err,
+			"output", strings.TrimSpace(output),
+			"site_name", c.config.SiteName)
+		// Cert is imported but binding failed — partial success
+		return &target.DeploymentResult{
+			Success:       false,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			DeployedAt:    time.Now(),
+			Metadata: map[string]string{
+				"thumbprint":     thumbprint,
+				"cert_store":     c.config.CertStore,
+				"import_success": "true",
+				"binding_error":  strings.TrimSpace(output),
+			},
+		}, fmt.Errorf("%s", errMsg)
+	}
 
 	deploymentDuration := time.Since(startTime)
-
-	c.logger.Warn("IIS deployment not yet implemented",
-		"site_name", c.config.SiteName)
+	c.logger.Info("certificate deployed to IIS successfully",
+		"duration", deploymentDuration.String(),
+		"site_name", c.config.SiteName,
+		"thumbprint", thumbprint)
 
 	return &target.DeploymentResult{
 		Success:       true,
 		TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
-		DeploymentID:  fmt.Sprintf("iis-%d", time.Now().Unix()),
-		Message:       "Certificate deployment to IIS initiated (stub)",
+		DeploymentID:  fmt.Sprintf("iis-%s-%d", thumbprint[:8], time.Now().Unix()),
+		Message:       "Certificate imported and IIS binding updated successfully",
 		DeployedAt:    time.Now(),
 		Metadata: map[string]string{
 			"hostname":    c.config.Hostname,
 			"site_name":   c.config.SiteName,
 			"cert_store":  c.config.CertStore,
+			"thumbprint":  thumbprint,
+			"port":        fmt.Sprintf("%d", port),
+			"sni":         fmt.Sprintf("%t", c.config.SNI),
 			"duration_ms": fmt.Sprintf("%d", deploymentDuration.Milliseconds()),
 		},
 	}, nil
 }
 
 // ValidateDeployment verifies that the certificate is properly deployed in IIS.
-// It checks the IIS binding configuration to ensure it's active with the correct certificate.
-//
-// TODO: Implement actual PowerShell validation.
-// PowerShell command:
-// - Get-IISSiteBinding -Name {SiteName} | Where {$_.protocol -eq "https"}
+// It checks the IIS binding to ensure it's active with the correct certificate thumbprint.
 func (c *Connector) ValidateDeployment(ctx context.Context, request target.ValidationRequest) (*target.ValidationResult, error) {
 	c.logger.Info("validating IIS deployment",
 		"certificate_id", request.CertificateID,
@@ -150,33 +450,211 @@ func (c *Connector) ValidateDeployment(ctx context.Context, request target.Valid
 
 	startTime := time.Now()
 
-	// TODO: Implement IIS deployment validation
-	// In production:
-	//   1. Query IIS binding status:
-	//      PowerShell: Get-WebBinding -Name "{SiteName}" -Protocol "https"
-	//   2. Verify binding exists and is active
-	//   3. Extract certificate thumbprint from binding
-	//   4. Query certificate store to verify thumbprint matches expected certificate
-	//   5. Check certificate validity dates and key match
+	port := c.config.Port
+	if port == 0 {
+		port = 443
+	}
 
+	// Query IIS binding for HTTPS on the configured port
+	bindingScript := fmt.Sprintf(
+		`$binding = Get-WebBinding -Name '%s' -Protocol 'https' -Port %d -ErrorAction SilentlyContinue; `+
+			`if ($binding) { $binding.certificateHash } else { 'NO_BINDING' }`,
+		c.config.SiteName, port,
+	)
+
+	output, err := c.executor.Execute(ctx, bindingScript)
+	if err != nil {
+		errMsg := fmt.Sprintf("failed to query IIS binding: %v (output: %s)", err, strings.TrimSpace(output))
+		c.logger.Error("validation failed", "error", err, "output", strings.TrimSpace(output))
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	bindingHash := strings.TrimSpace(output)
+	if bindingHash == "NO_BINDING" || bindingHash == "" {
+		errMsg := fmt.Sprintf("no HTTPS binding found on IIS site %q port %d", c.config.SiteName, port)
+		c.logger.Error("validation failed", "error", errMsg)
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	// Verify the certificate exists in the store
+	certCheckScript := fmt.Sprintf(
+		`$cert = Get-ChildItem -Path 'Cert:\LocalMachine\%s\%s' -ErrorAction SilentlyContinue; `+
+			`if ($cert -and $cert.NotAfter -gt (Get-Date)) { 'VALID' } `+
+			`elseif ($cert) { 'EXPIRED' } `+
+			`else { 'NOT_FOUND' }`,
+		c.config.CertStore, bindingHash,
+	)
+
+	output, err = c.executor.Execute(ctx, certCheckScript)
+	if err != nil {
+		errMsg := fmt.Sprintf("failed to verify certificate in store: %v", err)
+		c.logger.Error("validation failed", "error", err)
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+		}, fmt.Errorf("%s", errMsg)
+	}
+
+	certStatus := strings.TrimSpace(output)
 	validationDuration := time.Since(startTime)
 
-	c.logger.Warn("IIS validation not yet implemented",
-		"site_name", c.config.SiteName)
+	switch certStatus {
+	case "VALID":
+		c.logger.Info("IIS deployment validated successfully",
+			"duration", validationDuration.String(),
+			"thumbprint", bindingHash)
+		return &target.ValidationResult{
+			Valid:         true,
+			Serial:        request.Serial,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       "Certificate is bound to IIS site and valid",
+			ValidatedAt:   time.Now(),
+			Metadata: map[string]string{
+				"thumbprint":  bindingHash,
+				"site_name":   c.config.SiteName,
+				"cert_store":  c.config.CertStore,
+				"duration_ms": fmt.Sprintf("%d", validationDuration.Milliseconds()),
+			},
+		}, nil
 
-	return &target.ValidationResult{
-		Valid:         true,
-		Serial:        request.Serial,
-		TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
-		Message:       "Certificate deployment validation initiated (stub)",
-		ValidatedAt:   time.Now(),
-		Metadata: map[string]string{
-			"hostname":    c.config.Hostname,
-			"site_name":   c.config.SiteName,
-			"duration_ms": fmt.Sprintf("%d", validationDuration.Milliseconds()),
-		},
-	}, nil
+	case "EXPIRED":
+		errMsg := fmt.Sprintf("certificate %s is expired in store %q", bindingHash, c.config.CertStore)
+		c.logger.Error("validation failed: certificate expired", "thumbprint", bindingHash)
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+			Metadata: map[string]string{
+				"thumbprint": bindingHash,
+				"status":     "expired",
+			},
+		}, fmt.Errorf("%s", errMsg)
+
+	default: // NOT_FOUND or unexpected
+		errMsg := fmt.Sprintf("certificate %s not found in store %q", bindingHash, c.config.CertStore)
+		c.logger.Error("validation failed: certificate not in store", "thumbprint", bindingHash)
+		return &target.ValidationResult{
+			Valid:         false,
+			Serial:        request.Serial,
+			TargetAddress: fmt.Sprintf("%s (IIS: %s)", c.config.Hostname, c.config.SiteName),
+			Message:       errMsg,
+			ValidatedAt:   time.Now(),
+			Metadata: map[string]string{
+				"thumbprint": bindingHash,
+				"status":     "not_found",
+			},
+		}, fmt.Errorf("%s", errMsg)
+	}
 }
 
-// executePowerShellCommand will be implemented in V3 when IIS target connector ships.
-// Pattern: exec.CommandContext(ctx, "powershell", "-NoProfile", "-Command", psCommand)
+// createPFX converts PEM-encoded cert, key, and chain into PKCS#12 (PFX) format.
+// IIS requires PFX for certificate import. Uses go-pkcs12 Modern encoder
+// with strong encryption (same library used by M27 export service).
+func createPFX(certPEM, keyPEM, chainPEM string, password string) ([]byte, error) {
+	// Parse leaf certificate
+	certBlock, _ := pem.Decode([]byte(certPEM))
+	if certBlock == nil || certBlock.Type != "CERTIFICATE" {
+		return nil, fmt.Errorf("failed to decode certificate PEM")
+	}
+	leafCert, err := x509.ParseCertificate(certBlock.Bytes)
+	if err != nil {
+		return nil, fmt.Errorf("failed to parse leaf certificate: %w", err)
+	}
+
+	// Parse private key (supports PKCS#8, PKCS#1 RSA, and EC)
+	keyBlock, _ := pem.Decode([]byte(keyPEM))
+	if keyBlock == nil {
+		return nil, fmt.Errorf("failed to decode private key PEM")
+	}
+	privateKey, err := parsePrivateKey(keyBlock.Bytes)
+	if err != nil {
+		return nil, fmt.Errorf("failed to parse private key: %w", err)
+	}
+
+	// Parse CA chain certificates (optional)
+	var caCerts []*x509.Certificate
+	if chainPEM != "" {
+		rest := []byte(chainPEM)
+		for {
+			var block *pem.Block
+			block, rest = pem.Decode(rest)
+			if block == nil {
+				break
+			}
+			if block.Type != "CERTIFICATE" {
+				continue
+			}
+			caCert, err := x509.ParseCertificate(block.Bytes)
+			if err != nil {
+				return nil, fmt.Errorf("failed to parse CA certificate: %w", err)
+			}
+			caCerts = append(caCerts, caCert)
+		}
+	}
+
+	// Encode as PKCS#12 with Modern encryption
+	pfxData, err := pkcs12.Modern.Encode(privateKey, leafCert, caCerts, password)
+	if err != nil {
+		return nil, fmt.Errorf("failed to encode PKCS#12: %w", err)
+	}
+
+	return pfxData, nil
+}
+
+// parsePrivateKey attempts to parse a DER-encoded private key.
+// Tries PKCS#8, PKCS#1 RSA, and EC formats in order.
+func parsePrivateKey(der []byte) (interface{}, error) {
+	if key, err := x509.ParsePKCS8PrivateKey(der); err == nil {
+		return key, nil
+	}
+	if key, err := x509.ParsePKCS1PrivateKey(der); err == nil {
+		return key, nil
+	}
+	if key, err := x509.ParseECPrivateKey(der); err == nil {
+		return key, nil
+	}
+	return nil, fmt.Errorf("unsupported private key format")
+}
+
+// computeThumbprint calculates the SHA-1 thumbprint of a PEM-encoded certificate.
+// IIS uses SHA-1 thumbprints as the primary certificate identifier.
+// Returns uppercase hex string matching Windows certutil output.
+func computeThumbprint(certPEM string) (string, error) {
+	block, _ := pem.Decode([]byte(certPEM))
+	if block == nil || block.Type != "CERTIFICATE" {
+		return "", fmt.Errorf("failed to decode certificate PEM for thumbprint")
+	}
+	hash := sha1.Sum(block.Bytes)
+	return strings.ToUpper(hex.EncodeToString(hash[:])), nil
+}
+
+// generateRandomPassword creates a random alphanumeric password for transient PFX encryption.
+// The password is only used between PFX creation and import — it never persists.
+func generateRandomPassword(length int) (string, error) {
+	const charset = "abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789"
+	b := make([]byte, length)
+	if _, err := rand.Read(b); err != nil {
+		return "", fmt.Errorf("failed to read random bytes: %w", err)
+	}
+	for i := range b {
+		b[i] = charset[int(b[i])%len(charset)]
+	}
+	return string(b), nil
+}

internal/connector/target/iis/winrm.go

@@ -0,0 +1,89 @@
+package iis
+
+import (
+	"context"
+	"fmt"
+	"time"
+
+	"github.com/masterzen/winrm"
+)
+
+// WinRMConfig holds WinRM connection settings for remote IIS management.
+// Used when Mode is "winrm" — the proxy agent connects to a remote Windows
+// server over WinRM and executes PowerShell commands remotely.
+type WinRMConfig struct {
+	Host     string `json:"winrm_host"`     // WinRM target hostname or IP (required)
+	Port     int    `json:"winrm_port"`     // WinRM port (default 5985 for HTTP, 5986 for HTTPS)
+	Username string `json:"winrm_username"` // Windows user (e.g., "Administrator")
+	Password string `json:"winrm_password"` // Windows password
+	UseHTTPS bool   `json:"winrm_https"`    // Use HTTPS (port 5986) instead of HTTP (port 5985)
+	Insecure bool   `json:"winrm_insecure"` // Skip TLS certificate verification (for self-signed certs)
+	Timeout  int    `json:"winrm_timeout"`  // Operation timeout in seconds (default 60)
+}
+
+// winrmExecutor implements PowerShellExecutor by running PowerShell commands
+// on a remote Windows server via WinRM. This enables the proxy agent pattern:
+// a Linux agent in the same network zone manages Windows IIS servers remotely.
+type winrmExecutor struct {
+	client *winrm.Client
+}
+
+// newWinRMExecutor creates a WinRM client and returns a PowerShellExecutor.
+func newWinRMExecutor(cfg *WinRMConfig) (*winrmExecutor, error) {
+	if cfg.Host == "" {
+		return nil, fmt.Errorf("winrm_host is required for WinRM mode")
+	}
+	if cfg.Username == "" {
+		return nil, fmt.Errorf("winrm_username is required for WinRM mode")
+	}
+	if cfg.Password == "" {
+		return nil, fmt.Errorf("winrm_password is required for WinRM mode")
+	}
+
+	port := cfg.Port
+	if port == 0 {
+		if cfg.UseHTTPS {
+			port = 5986
+		} else {
+			port = 5985
+		}
+	}
+
+	timeout := time.Duration(cfg.Timeout) * time.Second
+	if cfg.Timeout == 0 {
+		timeout = 60 * time.Second
+	}
+
+	endpoint := winrm.NewEndpoint(
+		cfg.Host,
+		port,
+		cfg.UseHTTPS,
+		cfg.Insecure,
+		nil,  // CA cert
+		nil,  // Client cert
+		nil,  // Client key
+		timeout,
+	)
+
+	client, err := winrm.NewClient(endpoint, cfg.Username, cfg.Password)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create WinRM client: %w", err)
+	}
+
+	return &winrmExecutor{client: client}, nil
+}
+
+// Execute runs a PowerShell script on the remote Windows server via WinRM.
+// The script is wrapped in powershell.exe invocation on the remote side.
+func (e *winrmExecutor) Execute(ctx context.Context, script string) (string, error) {
+	// RunPSWithContext returns (stdout, stderr, exitCode, error)
+	stdout, stderr, exitCode, err := e.client.RunPSWithContext(ctx, script)
+	if err != nil {
+		return stdout + stderr, fmt.Errorf("WinRM command failed: %w", err)
+	}
+	if exitCode != 0 {
+		return stdout + stderr, fmt.Errorf("PowerShell exited with code %d: %s", exitCode, stdout+stderr)
+	}
+
+	return stdout, nil
+}

internal/connector/target/nginx/nginx.go

@@ -7,6 +7,7 @@ import (
 	"log/slog"
 	"os"
 	"os/exec"
+	"path/filepath"
 	"time"
 
 	"github.com/shankar0123/certctl/internal/connector/target"
@@ -67,13 +68,13 @@ func (c *Connector) ValidateConfig(ctx context.Context, rawConfig json.RawMessag
 		"chain_path", cfg.ChainPath)
 
 	// Verify directory exists and is writable
-	certDir := cfg.CertPath[:len(cfg.CertPath)-len("/cert.pem")] // Simple path extraction
+	certDir := filepath.Dir(cfg.CertPath)
 	if _, err := os.Stat(certDir); os.IsNotExist(err) {
 		return fmt.Errorf("NGINX cert directory does not exist: %s", certDir)
 	}
 
 	// Verify validate command works
-	cmd := exec.CommandContext(ctx, cfg.ValidateCommand)
+	cmd := exec.CommandContext(ctx, "sh", "-c", cfg.ValidateCommand)
 	if err := cmd.Run(); err != nil {
 		c.logger.Warn("NGINX config validation failed during config check",
 			"error", err,
@@ -115,20 +116,37 @@ func (c *Connector) DeployCertificate(ctx context.Context, request target.Deploy
 	}
 
 	// Write chain with same permissions
-	if err := os.WriteFile(c.config.ChainPath, []byte(request.ChainPEM), 0644); err != nil {
-		errMsg := fmt.Sprintf("failed to write chain: %v", err)
-		c.logger.Error("chain deployment failed", "error", err)
-		return &target.DeploymentResult{
-			Success:       false,
-			TargetAddress: c.config.ChainPath,
-			Message:       errMsg,
-			DeployedAt:    time.Now(),
-		}, fmt.Errorf("%s", errMsg)
+	if c.config.ChainPath != "" {
+		if err := os.WriteFile(c.config.ChainPath, []byte(request.ChainPEM), 0644); err != nil {
+			errMsg := fmt.Sprintf("failed to write chain: %v", err)
+			c.logger.Error("chain deployment failed", "error", err)
+			return &target.DeploymentResult{
+				Success:       false,
+				TargetAddress: c.config.ChainPath,
+				Message:       errMsg,
+				DeployedAt:    time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+	}
+
+	// Write private key if provided and key_path is configured
+	if c.config.KeyPath != "" && request.KeyPEM != "" {
+		if err := os.WriteFile(c.config.KeyPath, []byte(request.KeyPEM), 0600); err != nil {
+			errMsg := fmt.Sprintf("failed to write private key: %v", err)
+			c.logger.Error("key deployment failed", "error", err)
+			return &target.DeploymentResult{
+				Success:       false,
+				TargetAddress: c.config.KeyPath,
+				Message:       errMsg,
+				DeployedAt:    time.Now(),
+			}, fmt.Errorf("%s", errMsg)
+		}
+		c.logger.Info("private key written", "key_path", c.config.KeyPath)
 	}
 
 	// Validate NGINX configuration before reload
 	c.logger.Debug("validating NGINX configuration", "validate_command", c.config.ValidateCommand)
-	validateCmd := exec.CommandContext(ctx, c.config.ValidateCommand)
+	validateCmd := exec.CommandContext(ctx, "sh", "-c", c.config.ValidateCommand)
 	if output, err := validateCmd.CombinedOutput(); err != nil {
 		errMsg := fmt.Sprintf("NGINX config validation failed: %v (output: %s)", err, string(output))
 		c.logger.Error("NGINX validation failed", "error", err, "output", string(output))
@@ -142,7 +160,7 @@ func (c *Connector) DeployCertificate(ctx context.Context, request target.Deploy
 
 	// Reload NGINX
 	c.logger.Debug("reloading NGINX", "reload_command", c.config.ReloadCommand)
-	reloadCmd := exec.CommandContext(ctx, c.config.ReloadCommand)
+	reloadCmd := exec.CommandContext(ctx, "sh", "-c", c.config.ReloadCommand)
 	if output, err := reloadCmd.CombinedOutput(); err != nil {
 		errMsg := fmt.Sprintf("NGINX reload failed: %v (output: %s)", err, string(output))
 		c.logger.Error("NGINX reload failed", "error", err, "output", string(output))
@@ -187,7 +205,7 @@ func (c *Connector) ValidateDeployment(ctx context.Context, request target.Valid
 	startTime := time.Now()
 
 	// Validate NGINX configuration
-	validateCmd := exec.CommandContext(ctx, c.config.ValidateCommand)
+	validateCmd := exec.CommandContext(ctx, "sh", "-c", c.config.ValidateCommand)
 	if err := validateCmd.Run(); err != nil {
 		errMsg := fmt.Sprintf("NGINX config validation failed: %v", err)
 		c.logger.Error("validation failed", "error", err)

internal/domain/connector.go

@@ -84,4 +84,5 @@ const (
 	TargetTypeIIS      TargetType = "IIS"
 	TargetTypeTraefik  TargetType = "Traefik"
 	TargetTypeCaddy    TargetType = "Caddy"
+	TargetTypeEnvoy    TargetType = "Envoy"
 )

internal/service/agent.go

@@ -178,14 +178,15 @@ func (s *AgentService) SubmitCSR(ctx context.Context, agentID string, certID str
 			}
 
 			version := &domain.CertificateVersion{
-				ID:            generateID("certver"),
-				CertificateID: certID,
-				SerialNumber:  result.Serial,
-				NotBefore:     result.NotBefore,
-				NotAfter:      result.NotAfter,
-				PEMChain:      result.CertPEM + "\n" + result.ChainPEM,
-				CSRPEM:        string(csrPEM),
-				CreatedAt:     time.Now(),
+				ID:                generateID("certver"),
+				CertificateID:     certID,
+				SerialNumber:      result.Serial,
+				NotBefore:         result.NotBefore,
+				NotAfter:          result.NotAfter,
+				FingerprintSHA256: computeCertFingerprint(result.CertPEM),
+				PEMChain:          result.CertPEM + "\n" + result.ChainPEM,
+				CSRPEM:            string(csrPEM),
+				CreatedAt:         time.Now(),
 			}
 
 			if err := s.certRepo.CreateVersion(ctx, version); err != nil {

internal/service/certificate.go

@@ -14,10 +14,12 @@ import (
 type CertificateService struct {
 	certRepo       repository.CertificateRepository
 	targetRepo     repository.TargetRepository
+	jobRepo        repository.JobRepository
 	policyService  *PolicyService
 	auditService   *AuditService
 	revSvc         *RevocationSvc
 	caSvc          *CAOperationsSvc
+	keygenMode     string
 }
 
 // NewCertificateService creates a new certificate service.
@@ -48,6 +50,16 @@ func (s *CertificateService) SetTargetRepo(repo repository.TargetRepository) {
 	s.targetRepo = repo
 }
 
+// SetJobRepo sets the job repository for creating renewal/issuance jobs.
+func (s *CertificateService) SetJobRepo(repo repository.JobRepository) {
+	s.jobRepo = repo
+}
+
+// SetKeygenMode sets the key generation mode (agent or server).
+func (s *CertificateService) SetKeygenMode(mode string) {
+	s.keygenMode = mode
+}
+
 // List returns a paginated list of certificates matching the filter.
 func (s *CertificateService) List(ctx context.Context, filter *repository.CertificateFilter) ([]*domain.ManagedCertificate, int, error) {
 	certs, total, err := s.certRepo.List(ctx, filter)
@@ -195,6 +207,8 @@ func (s *CertificateService) GetVersions(ctx context.Context, certID string) ([]
 }
 
 // TriggerRenewalWithActor initiates a renewal job if the certificate is eligible.
+// Creates a Renewal job (or Issuance for new certs) so the scheduler's job processor
+// can pick it up and route it through the issuer connector.
 func (s *CertificateService) TriggerRenewalWithActor(ctx context.Context, certID string, actor string) error {
 	cert, err := s.certRepo.Get(ctx, certID)
 	if err != nil {
@@ -220,6 +234,45 @@ func (s *CertificateService) TriggerRenewalWithActor(ctx context.Context, certID
 		return fmt.Errorf("failed to update certificate status: %w", err)
 	}
 
+	// Create a renewal job so the job processor can pick it up.
+	// In agent keygen mode, the job starts as AwaitingCSR so the agent
+	// generates the key pair and submits a CSR. In server mode, it starts as Pending.
+	if s.jobRepo != nil {
+		jobStatus := domain.JobStatusPending
+		if s.keygenMode == "agent" {
+			jobStatus = domain.JobStatusAwaitingCSR
+		}
+
+		// Determine job type: Issuance for certs that have never been issued,
+		// Renewal for certs that already have a version.
+		jobType := domain.JobTypeRenewal
+		if cert.ExpiresAt.IsZero() || cert.ExpiresAt.Year() < 2000 {
+			jobType = domain.JobTypeIssuance
+		}
+
+		job := &domain.Job{
+			ID:            generateID("job"),
+			CertificateID: cert.ID,
+			Type:          jobType,
+			Status:        jobStatus,
+			MaxAttempts:   3,
+			ScheduledAt:   time.Now(),
+			CreatedAt:     time.Now(),
+		}
+
+		if err := s.jobRepo.Create(ctx, job); err != nil {
+			slog.Error("failed to create renewal job", "cert_id", cert.ID, "error", err)
+			return fmt.Errorf("failed to create renewal job: %w", err)
+		}
+
+		slog.Info("created renewal job via API trigger",
+			"job_id", job.ID,
+			"cert_id", cert.ID,
+			"job_type", string(jobType),
+			"job_status", string(jobStatus),
+			"keygen_mode", s.keygenMode)
+	}
+
 	// Record audit event
 	if err := s.auditService.RecordEvent(ctx, actor, domain.ActorTypeUser,
 		"renewal_triggered", "certificate", certID,
@@ -304,6 +357,14 @@ func (s *CertificateService) CreateCertificate(cert domain.ManagedCertificate) (
 	if cert.UpdatedAt.IsZero() {
 		cert.UpdatedAt = now
 	}
+	// Default status to Pending if not set (DB column DEFAULT only applies when column is omitted from INSERT)
+	if cert.Status == "" {
+		cert.Status = domain.CertificateStatusPending
+	}
+	// Default tags to empty map if nil (avoids JSON null in JSONB column)
+	if cert.Tags == nil {
+		cert.Tags = make(map[string]string)
+	}
 	if err := s.certRepo.Create(context.Background(), &cert); err != nil {
 		return nil, fmt.Errorf("failed to create certificate: %w", err)
 	}

internal/service/job.go

@@ -54,6 +54,16 @@ func (s *JobService) ProcessPendingJobs(ctx context.Context) error {
 
 	// Process each job
 	for _, job := range pendingJobs {
+		// Skip deployment jobs that have an agent_id — those are meant for agent
+		// pickup via GetPendingWork(), not server-side processing. The server should
+		// only process deployment jobs without an agent (legacy/serverless targets).
+		if job.Type == domain.JobTypeDeployment && job.AgentID != nil && *job.AgentID != "" {
+			s.logger.Debug("skipping agent-routed deployment job",
+				"job_id", job.ID,
+				"agent_id", *job.AgentID)
+			continue
+		}
+
 		if err := s.processJob(ctx, job); err != nil {
 			s.logger.Error("failed to process job",
 				"job_id", job.ID,

internal/service/renewal.go

@@ -636,23 +636,50 @@ func (s *RenewalService) CompleteAgentCSRRenewal(ctx context.Context, job *domai
 }
 
 // createDeploymentJobs creates pending deployment jobs for each target associated with a cert.
+// If cert.TargetIDs is empty (common — the repository doesn't populate this field),
+// falls back to querying certificate_target_mappings via targetRepo.ListByCertificate.
 func (s *RenewalService) createDeploymentJobs(ctx context.Context, cert *domain.ManagedCertificate) {
-	if len(cert.TargetIDs) == 0 {
+	// Resolve targets: prefer in-memory TargetIDs, fall back to DB query
+	type targetInfo struct {
+		id      string
+		agentID string
+	}
+	var targets []targetInfo
+
+	if len(cert.TargetIDs) > 0 {
+		// TargetIDs populated (e.g. from test or manual wiring)
+		for _, tid := range cert.TargetIDs {
+			ti := targetInfo{id: tid}
+			if s.targetRepo != nil {
+				if target, err := s.targetRepo.Get(ctx, tid); err == nil && target.AgentID != "" {
+					ti.agentID = target.AgentID
+				}
+			}
+			targets = append(targets, ti)
+		}
+	} else if s.targetRepo != nil {
+		// TargetIDs empty — query certificate_target_mappings via repository
+		dbTargets, err := s.targetRepo.ListByCertificate(ctx, cert.ID)
+		if err != nil {
+			slog.Error("failed to query targets for certificate", "cert_id", cert.ID, "error", err)
+			return
+		}
+		for _, t := range dbTargets {
+			targets = append(targets, targetInfo{id: t.ID, agentID: t.AgentID})
+		}
+	}
+
+	if len(targets) == 0 {
+		slog.Debug("no targets found for certificate, skipping deployment", "cert_id", cert.ID)
 		return
 	}
-	for _, targetID := range cert.TargetIDs {
-		tid := targetID
 
-		// Resolve agent_id from target for job routing
+	for _, t := range targets {
+		tid := t.id
 		var agentIDPtr *string
-		if s.targetRepo != nil {
-			target, err := s.targetRepo.Get(ctx, tid)
-			if err != nil {
-				slog.Warn("failed to resolve agent for deployment job", "target_id", tid, "error", err)
-			} else if target.AgentID != "" {
-				agentID := target.AgentID
-				agentIDPtr = &agentID
-			}
+		if t.agentID != "" {
+			aid := t.agentID
+			agentIDPtr = &aid
 		}
 
 		deployJob := &domain.Job{
@@ -667,7 +694,9 @@ func (s *RenewalService) createDeploymentJobs(ctx context.Context, cert *domain.
 			CreatedAt:     time.Now(),
 		}
 		if err := s.jobRepo.Create(ctx, deployJob); err != nil {
-			slog.Error("failed to create deployment job for target", "target_id", targetID, "error", err)
+			slog.Error("failed to create deployment job for target", "target_id", tid, "cert_id", cert.ID, "error", err)
+		} else {
+			slog.Info("created deployment job", "job_id", deployJob.ID, "cert_id", cert.ID, "target_id", tid, "agent_id", t.agentID)
 		}
 	}
 }

migrations/seed_test.sql

@@ -0,0 +1,143 @@
+-- =============================================================================
+-- certctl Test Environment — Seed Data
+-- =============================================================================
+--
+-- Pre-populates the database with the minimum objects needed to test the full
+-- certificate lifecycle against real CA backends (Pebble, step-ca, Local CA).
+--
+-- Load order (handled by Docker entrypoint filename sorting):
+--   001_schema.sql → ... → 008_verification.sql → 010_seed.sql → 015_seed_test.sql
+--
+-- All IDs use a "test-" prefix so they're easy to spot in the dashboard.
+-- =============================================================================
+
+-- ---------------------------------------------------------------------------
+-- Team
+-- ---------------------------------------------------------------------------
+INSERT INTO teams (id, name, description)
+VALUES (
+  'team-test-ops',
+  'Test Operations',
+  'Operations team for certctl testing environment'
+) ON CONFLICT (id) DO NOTHING;
+
+-- ---------------------------------------------------------------------------
+-- Owner (references team)
+-- ---------------------------------------------------------------------------
+INSERT INTO owners (id, name, email, team_id)
+VALUES (
+  'owner-test-admin',
+  'Test Admin',
+  'admin@certctl-test.local',
+  'team-test-ops'
+) ON CONFLICT (id) DO NOTHING;
+
+-- ---------------------------------------------------------------------------
+-- Agent — must exist before the agent binary sends its first heartbeat
+-- ---------------------------------------------------------------------------
+-- The agent binary (certctl-agent container) connects with:
+--   CERTCTL_AGENT_ID=agent-test-01
+--   CERTCTL_AGENT_NAME=test-agent-01
+-- The heartbeat handler does a GET by ID — if the agent doesn't exist, it 404s.
+-- api_key_hash is SHA-256 of "test-agent-key-2026" (not used for auth, just stored).
+INSERT INTO agents (id, name, hostname, status, registered_at, api_key_hash, os, architecture, ip_address, version)
+VALUES (
+  'agent-test-01',
+  'test-agent-01',
+  'certctl-test-agent',
+  'online',
+  NOW(),
+  'cad819dee454889f686d678f691e5084e58ba149762eae2fda4d0bd2abaceefa',
+  'linux',
+  'amd64',
+  '10.30.50.8',
+  'test'
+) ON CONFLICT (id) DO NOTHING;
+
+-- The network scanner uses "server-scanner" as a virtual agent.
+-- It gets auto-created by the server code, but seed it here to avoid races.
+INSERT INTO agents (id, name, hostname, status, registered_at, api_key_hash)
+VALUES (
+  'server-scanner',
+  'server-scanner',
+  'certctl-server',
+  'online',
+  NOW(),
+  'no-key'
+) ON CONFLICT (id) DO NOTHING;
+
+-- ---------------------------------------------------------------------------
+-- Issuers — one row per CA backend in the test environment
+-- ---------------------------------------------------------------------------
+-- These are metadata records the dashboard reads. The actual CA connections
+-- are configured via env vars on the server container.
+
+-- Local CA (self-signed, always available)
+INSERT INTO issuers (id, name, type, config, enabled)
+VALUES (
+  'iss-local',
+  'Local CA (Self-Signed)',
+  'local',
+  '{"mode": "self-signed", "description": "Built-in self-signed CA for testing"}'::jsonb,
+  true
+) ON CONFLICT (id) DO NOTHING;
+
+-- ACME via Pebble (simulates Let''s Encrypt)
+INSERT INTO issuers (id, name, type, config, enabled)
+VALUES (
+  'iss-acme-staging',
+  'ACME (Pebble Test CA)',
+  'acme',
+  '{"directory_url": "https://pebble:14000/dir", "email": "test@certctl.dev", "challenge_type": "http-01", "description": "Pebble ACME test server simulating Lets Encrypt"}'::jsonb,
+  true
+) ON CONFLICT (id) DO NOTHING;
+
+-- step-ca (Smallstep private CA)
+INSERT INTO issuers (id, name, type, config, enabled)
+VALUES (
+  'iss-stepca',
+  'step-ca (Private CA)',
+  'stepca',
+  '{"url": "https://step-ca:9000", "provisioner": "admin", "description": "Smallstep private CA with JWK provisioner"}'::jsonb,
+  true
+) ON CONFLICT (id) DO NOTHING;
+
+-- ---------------------------------------------------------------------------
+-- Certificate Profile — TLS server certs, 90-day max
+-- ---------------------------------------------------------------------------
+INSERT INTO certificate_profiles (id, name, description, max_ttl_seconds, allowed_ekus, allowed_key_algorithms)
+VALUES (
+  'prof-test-tls',
+  'Test TLS Server',
+  'Standard TLS server certificate profile for testing',
+  7776000,  -- 90 days
+  '["serverAuth"]'::jsonb,
+  '[{"algorithm": "ECDSA", "min_size": 256}, {"algorithm": "RSA", "min_size": 2048}]'::jsonb
+) ON CONFLICT (id) DO NOTHING;
+
+-- ---------------------------------------------------------------------------
+-- Certificate Profile — S/MIME email protection
+-- ---------------------------------------------------------------------------
+INSERT INTO certificate_profiles (id, name, description, max_ttl_seconds, allowed_ekus, allowed_key_algorithms)
+VALUES (
+  'prof-test-smime',
+  'Test S/MIME Email',
+  'S/MIME certificate profile for email signing and encryption',
+  31536000,  -- 365 days
+  '["emailProtection"]'::jsonb,
+  '[{"algorithm": "ECDSA", "min_size": 256}, {"algorithm": "RSA", "min_size": 2048}]'::jsonb
+) ON CONFLICT (id) DO NOTHING;
+
+-- ---------------------------------------------------------------------------
+-- Deployment Target — NGINX (references agent-test-01)
+-- ---------------------------------------------------------------------------
+-- The agent deploys certs to NGINX via the shared nginx_certs volume.
+INSERT INTO deployment_targets (id, name, type, agent_id, config, enabled)
+VALUES (
+  'target-test-nginx',
+  'Test NGINX',
+  'NGINX',
+  'agent-test-01',
+  '{"cert_path": "/nginx-certs/cert.pem", "key_path": "/nginx-certs/key.pem", "chain_path": "/nginx-certs/chain.pem", "reload_command": "true", "validate_command": "true"}'::jsonb,
+  true
+) ON CONFLICT (id) DO NOTHING;

web/src/api/client.test.ts

@@ -83,6 +83,12 @@ import {
   getIssuer,
   getTarget,
   getPrometheusMetrics,
+  getCertificateDeployments,
+  getCRL,
+  getOCSPStatus,
+  updateIssuer,
+  updateTarget,
+  getPolicy,
 } from './client';
 
 // Mock global fetch
@@ -632,6 +638,50 @@ describe('API Client', () => {
       expect(url).toBe('/api/v1/issuers');
       expect(init.method).toBe('POST');
     });
+
+    it('createIssuer sends correct payload for VaultPKI type', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ id: 'iss-vault', name: 'Vault PKI' }));
+      const vaultPayload = {
+        name: 'Vault PKI',
+        type: 'VaultPKI',
+        config: {
+          addr: 'https://vault.internal:8200',
+          token: 'hvs.test-token',
+          mount: 'pki',
+          role: 'web-certs',
+          ttl: '8760h',
+        },
+      };
+      await createIssuer(vaultPayload);
+      const [url, init] = mockFetch.mock.calls[0];
+      expect(url).toBe('/api/v1/issuers');
+      expect(init.method).toBe('POST');
+      const body = JSON.parse(init.body);
+      expect(body.type).toBe('VaultPKI');
+      expect(body.config.addr).toBe('https://vault.internal:8200');
+      expect(body.config.role).toBe('web-certs');
+    });
+
+    it('createIssuer sends correct payload for DigiCert type', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ id: 'iss-digicert', name: 'DigiCert' }));
+      const digicertPayload = {
+        name: 'DigiCert CertCentral',
+        type: 'DigiCert',
+        config: {
+          api_key: 'test-api-key',
+          org_id: '12345',
+          product_type: 'ssl_basic',
+        },
+      };
+      await createIssuer(digicertPayload);
+      const [url, init] = mockFetch.mock.calls[0];
+      expect(url).toBe('/api/v1/issuers');
+      expect(init.method).toBe('POST');
+      const body = JSON.parse(init.body);
+      expect(body.type).toBe('DigiCert');
+      expect(body.config.org_id).toBe('12345');
+      expect(body.config.product_type).toBe('ssl_basic');
+    });
   });
 
   // ─── Audit ──────────────────────────────────────────
@@ -1106,4 +1156,53 @@ describe('API Client', () => {
       expect(init.headers['Authorization']).toBe('Bearer prom-key');
     });
   });
+
+  describe('Frontend Audit: New API Functions', () => {
+    it('getCertificateDeployments sends GET with cert ID', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ data: [], total: 0 }));
+      await getCertificateDeployments('mc-1');
+      expect(mockFetch.mock.calls[0][0]).toContain('/api/v1/certificates/mc-1/deployments');
+    });
+
+    it('getCRL sends GET to /crl', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ entries: [], total: 0 }));
+      await getCRL();
+      expect(mockFetch.mock.calls[0][0]).toBe('/api/v1/crl');
+    });
+
+    it('getOCSPStatus sends GET with issuer and serial', async () => {
+      const buf = new ArrayBuffer(8);
+      mockFetch.mockReturnValueOnce(
+        Promise.resolve({
+          ok: true,
+          status: 200,
+          arrayBuffer: () => Promise.resolve(buf),
+        } as Response)
+      );
+      await getOCSPStatus('iss-local', 'ABC123');
+      expect(mockFetch.mock.calls[0][0]).toBe('/api/v1/ocsp/iss-local/ABC123');
+    });
+
+    it('updateIssuer sends PUT with data', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ id: 'iss-1', name: 'Updated' }));
+      await updateIssuer('iss-1', { name: 'Updated' });
+      const [url, init] = mockFetch.mock.calls[0];
+      expect(url).toBe('/api/v1/issuers/iss-1');
+      expect(init.method).toBe('PUT');
+    });
+
+    it('updateTarget sends PUT with data', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ id: 't-1', name: 'Updated' }));
+      await updateTarget('t-1', { name: 'Updated' });
+      const [url, init] = mockFetch.mock.calls[0];
+      expect(url).toBe('/api/v1/targets/t-1');
+      expect(init.method).toBe('PUT');
+    });
+
+    it('getPolicy sends GET with policy ID', async () => {
+      mockFetch.mockReturnValueOnce(mockJsonResponse({ id: 'pol-1', name: 'Test' }));
+      await getPolicy('pol-1');
+      expect(mockFetch.mock.calls[0][0]).toBe('/api/v1/policies/pol-1');
+    });
+  });
 });

web/src/api/client.ts

@@ -122,6 +122,26 @@ export const exportCertificatePKCS12 = (id: string, password: string = '') => {
   });
 };
 
+// Certificate Deployments
+export const getCertificateDeployments = (id: string, params: Record<string, string> = {}) => {
+  const qs = new URLSearchParams({ page: '1', per_page: '50', ...params }).toString();
+  return fetchJSON<PaginatedResponse<Job>>(`${BASE}/certificates/${id}/deployments?${qs}`);
+};
+
+// CRL / OCSP
+export const getCRL = () =>
+  fetchJSON<{ version: number; entries: unknown[]; total: number; generated_at: string }>(`${BASE}/crl`);
+
+export const getOCSPStatus = (issuerId: string, serial: string) => {
+  const headers: Record<string, string> = {};
+  if (apiKey) headers['Authorization'] = `Bearer ${apiKey}`;
+  return fetch(`${BASE}/ocsp/${issuerId}/${serial}`, { headers })
+    .then(r => {
+      if (!r.ok) throw new Error(`OCSP request failed: ${r.status}`);
+      return r.arrayBuffer();
+    });
+};
+
 // Agents
 export const getAgents = (params: Record<string, string> = {}) => {
   const qs = new URLSearchParams({ page: '1', per_page: '50', ...params }).toString();
@@ -170,6 +190,9 @@ export const createPolicy = (data: Partial<PolicyRule>) =>
 export const updatePolicy = (id: string, data: Partial<PolicyRule>) =>
   fetchJSON<PolicyRule>(`${BASE}/policies/${id}`, { method: 'PUT', body: JSON.stringify(data) });
 
+export const getPolicy = (id: string) =>
+  fetchJSON<PolicyRule>(`${BASE}/policies/${id}`);
+
 export const deletePolicy = (id: string) =>
   fetchJSON<{ message: string }>(`${BASE}/policies/${id}`, { method: 'DELETE' });
 
@@ -188,6 +211,9 @@ export const createIssuer = (data: Partial<Issuer>) =>
 export const testIssuerConnection = (id: string) =>
   fetchJSON<{ message: string }>(`${BASE}/issuers/${id}/test`, { method: 'POST' });
 
+export const updateIssuer = (id: string, data: Partial<Issuer>) =>
+  fetchJSON<Issuer>(`${BASE}/issuers/${id}`, { method: 'PUT', body: JSON.stringify(data) });
+
 export const deleteIssuer = (id: string) =>
   fetchJSON<{ message: string }>(`${BASE}/issuers/${id}`, { method: 'DELETE' });
 
@@ -200,6 +226,9 @@ export const getTargets = (params: Record<string, string> = {}) => {
 export const createTarget = (data: Partial<Target>) =>
   fetchJSON<Target>(`${BASE}/targets`, { method: 'POST', body: JSON.stringify(data) });
 
+export const updateTarget = (id: string, data: Partial<Target>) =>
+  fetchJSON<Target>(`${BASE}/targets/${id}`, { method: 'PUT', body: JSON.stringify(data) });
+
 export const deleteTarget = (id: string) =>
   fetchJSON<{ message: string }>(`${BASE}/targets/${id}`, { method: 'DELETE' });
 

web/src/api/types.ts

@@ -18,7 +18,10 @@ export interface Certificate {
   expires_at: string;
   revoked_at?: string;
   revocation_reason?: string;
+  target_ids?: string[];
   tags: Record<string, string>;
+  last_renewal_at?: string;
+  last_deployment_at?: string;
   created_at: string;
   updated_at: string;
 }
@@ -45,6 +48,8 @@ export interface CertificateVersion {
   csr_pem: string;
   not_before: string;
   not_after: string;
+  key_algorithm?: string;
+  key_size?: number;
   created_at: string;
 }
 
@@ -135,7 +140,10 @@ export interface Issuer {
   type: string;
   config: Record<string, unknown>;
   status: string;
+  /** Backend returns enabled boolean; status is derived from this */
+  enabled: boolean;
   created_at: string;
+  updated_at?: string;
 }
 
 export interface Target {
@@ -147,6 +155,7 @@ export interface Target {
   config: Record<string, unknown>;
   status: string;
   created_at: string;
+  updated_at?: string;
 }
 
 export interface KeyAlgorithmRule {

web/src/components/Layout.tsx

@@ -71,7 +71,7 @@ export default function Layout() {
         </nav>
 
         <div className="px-5 py-3 border-t border-white/10 flex items-center justify-between">
-          <span className="text-[10px] text-brand-300/60 font-mono">v2.0.14</span>
+          <span className="text-[10px] text-brand-300/60 font-mono">v2.0.20</span>
           {authRequired && (
             <button
               onClick={logout}

web/src/components/StatusBadge.tsx

@@ -23,6 +23,9 @@ const statusStyles: Record<string, string> = {
   Unmanaged:           'badge-warning',
   Managed:             'badge-success',
   Dismissed:           'badge-neutral',
+  // Issuer statuses
+  Enabled:             'badge-success',
+  Disabled:            'badge-neutral',
   // Notification statuses
   sent:                'badge-success',
   pending:             'badge-warning',

web/src/components/issuer/ConfigDetailModal.tsx

@@ -0,0 +1,56 @@
+/**
+ * Full config viewer modal with sensitive field redaction.
+ * Replaces the 60-char truncation in the issuers table.
+ * Reusable for targets in M35 — no IssuersPage-specific imports.
+ */
+import { isSensitiveKey } from '../../config/issuerTypes';
+
+interface ConfigDetailModalProps {
+  title: string;
+  config: Record<string, unknown>;
+  onClose: () => void;
+}
+
+export default function ConfigDetailModal({ title, config, onClose }: ConfigDetailModalProps) {
+  const entries = Object.entries(config);
+
+  return (
+    <div className="fixed inset-0 bg-black bg-opacity-50 z-50 flex items-center justify-center">
+      <div className="bg-surface border border-surface-border rounded-lg shadow-lg max-w-lg w-full mx-4">
+        <div className="border-b border-surface-border px-6 py-4 flex justify-between items-center">
+          <h2 className="text-lg font-semibold text-ink">{title}</h2>
+          <button onClick={onClose} className="text-ink-muted hover:text-ink transition-colors">
+            ✕
+          </button>
+        </div>
+        <div className="px-6 py-4 max-h-96 overflow-y-auto">
+          {entries.length === 0 ? (
+            <div className="text-sm text-ink-faint py-4 text-center">No configuration data</div>
+          ) : (
+            <div className="space-y-0">
+              {entries.map(([key, val]) => {
+                const redacted = isSensitiveKey(key);
+                return (
+                  <div key={key} className="flex justify-between py-2 border-b border-surface-border/50">
+                    <span className="text-sm text-ink-muted">{key}</span>
+                    <span className="text-sm text-ink font-mono text-right max-w-xs break-all">
+                      {redacted ? '********' : String(val ?? '')}
+                    </span>
+                  </div>
+                );
+              })}
+            </div>
+          )}
+        </div>
+        <div className="border-t border-surface-border px-6 py-4 flex justify-end">
+          <button
+            onClick={onClose}
+            className="px-4 py-2 border border-surface-border rounded text-ink hover:bg-surface-hover transition-colors text-sm font-medium"
+          >
+            Close
+          </button>
+        </div>
+      </div>
+    </div>
+  );
+}

web/src/components/issuer/ConfigForm.tsx

@@ -0,0 +1,139 @@
+/**
+ * Renders config fields from an IssuerTypeConfig.configFields definition.
+ * Handles sensitive field masking. M34 will reuse this directly for its
+ * dynamic config wizard. M35 can reuse it for target config forms.
+ */
+import type { ConfigField } from '../../config/issuerTypes';
+
+interface ConfigFormProps {
+  fields: ConfigField[];
+  values: Record<string, unknown>;
+  onChange: (key: string, value: unknown) => void;
+  /** When true, sensitive fields show as ******** with a "Change" button.
+   *  Used in edit mode — empty value means "keep existing". */
+  editMode?: boolean;
+}
+
+export default function ConfigForm({ fields, values, onChange, editMode }: ConfigFormProps) {
+  return (
+    <div className="space-y-5">
+      {fields.map((field) => (
+        <ConfigFieldInput
+          key={field.key}
+          field={field}
+          value={values[field.key]}
+          onChange={(v) => onChange(field.key, v)}
+          editMode={editMode}
+        />
+      ))}
+    </div>
+  );
+}
+
+function ConfigFieldInput({
+  field,
+  value,
+  onChange,
+  editMode,
+}: {
+  field: ConfigField;
+  value: unknown;
+  onChange: (v: unknown) => void;
+  editMode?: boolean;
+}) {
+  const inputCls =
+    'w-full px-3 py-2 bg-surface border border-surface-border rounded text-ink placeholder-ink-faint focus:outline-none focus:border-brand-500 transition-colors';
+
+  // In edit mode, sensitive fields that haven't been touched show as masked
+  if (editMode && field.sensitive && value === undefined) {
+    return (
+      <div>
+        <FieldLabel field={field} />
+        <div className="flex items-center gap-2">
+          <span className="text-sm text-ink-muted font-mono">********</span>
+          <button
+            type="button"
+            onClick={() => onChange('')}
+            className="text-xs text-brand-400 hover:text-brand-500"
+          >
+            Change
+          </button>
+        </div>
+      </div>
+    );
+  }
+
+  if (field.type === 'select') {
+    return (
+      <div>
+        <FieldLabel field={field} />
+        <select
+          value={(value as string) || ''}
+          onChange={(e) => onChange(e.target.value)}
+          className={inputCls}
+        >
+          <option value="">Select {field.label}</option>
+          {field.options?.map((opt) => (
+            <option key={opt} value={opt}>{opt}</option>
+          ))}
+        </select>
+      </div>
+    );
+  }
+
+  if (field.type === 'textarea') {
+    return (
+      <div>
+        <FieldLabel field={field} />
+        <textarea
+          value={(value as string) || ''}
+          onChange={(e) => onChange(e.target.value)}
+          placeholder={field.placeholder}
+          rows={4}
+          className={`${inputCls} font-mono text-xs`}
+        />
+      </div>
+    );
+  }
+
+  if (field.type === 'number') {
+    return (
+      <div>
+        <FieldLabel field={field} />
+        <input
+          type="number"
+          value={(value as number | string) ?? ''}
+          onChange={(e) => onChange(e.target.value ? parseInt(e.target.value, 10) : '')}
+          placeholder={field.placeholder}
+          className={inputCls}
+        />
+      </div>
+    );
+  }
+
+  // text or password
+  return (
+    <div>
+      <FieldLabel field={field} />
+      <input
+        type={field.type === 'password' ? 'password' : 'text'}
+        value={(value as string) || ''}
+        onChange={(e) => onChange(e.target.value)}
+        placeholder={field.placeholder}
+        className={inputCls}
+      />
+    </div>
+  );
+}
+
+function FieldLabel({ field }: { field: ConfigField }) {
+  return (
+    <label className="block text-sm font-medium text-ink mb-2">
+      {field.label}
+      {field.required && <span className="text-red-600 ml-1">*</span>}
+      {field.sensitive && (
+        <span className="ml-2 text-xs text-yellow-500 font-normal">sensitive</span>
+      )}
+    </label>
+  );
+}

web/src/components/issuer/TypeSelector.tsx

@@ -0,0 +1,35 @@
+/**
+ * Issuer type selector grid. Used in both the catalog view and create wizard.
+ * M34 will reuse this for its 3-step wizard (Select Type step).
+ */
+import { issuerTypes, type IssuerTypeConfig } from '../../config/issuerTypes';
+
+interface TypeSelectorProps {
+  onSelect: (typeId: string) => void;
+  /** Filter to only show these type IDs. If not provided, shows all non-comingSoon types. */
+  filterIds?: string[];
+}
+
+export default function TypeSelector({ onSelect, filterIds }: TypeSelectorProps) {
+  const types = filterIds
+    ? issuerTypes.filter(t => filterIds.includes(t.id))
+    : issuerTypes.filter(t => !t.comingSoon);
+
+  return (
+    <div className="grid grid-cols-2 gap-4">
+      {types.map((type: IssuerTypeConfig) => (
+        <button
+          key={type.id}
+          onClick={() => onSelect(type.id)}
+          className="p-4 border border-surface-border rounded-lg hover:border-brand-500 hover:bg-opacity-5 transition-all text-left"
+        >
+          <div className="flex items-center gap-2">
+            <span className="text-lg">{type.icon}</span>
+            <span className="font-medium text-ink">{type.name}</span>
+          </div>
+          <div className="text-sm text-ink-muted mt-1">{type.description}</div>
+        </button>
+      ))}
+    </div>
+  );
+}

web/src/config/issuerTypes.ts

@@ -0,0 +1,179 @@
+/**
+ * Shared issuer type configuration.
+ * Imported by IssuersPage.tsx (M33), and will be reused by M34 (Dynamic Issuer Config)
+ * for its 3-step wizard config forms.
+ */
+
+export interface ConfigField {
+  key: string;
+  label: string;
+  type?: 'text' | 'password' | 'number' | 'select' | 'textarea';
+  placeholder?: string;
+  required: boolean;
+  options?: string[];
+  defaultValue?: string;
+  /** Mark fields that contain secrets (tokens, keys, passwords).
+   *  Display as ******** when viewing existing config. M34 will use this
+   *  for AES-GCM encryption decisions. */
+  sensitive?: boolean;
+}
+
+export interface IssuerTypeConfig {
+  id: string;
+  name: string;
+  description: string;
+  icon: string;
+  configFields: ConfigField[];
+  /** If true, this type is not yet implemented — show as "Coming Soon" */
+  comingSoon?: boolean;
+}
+
+/**
+ * Canonical type label map. Keys match what the backend API returns.
+ * DB stores: local, acme, stepca, openssl, VaultPKI, DigiCert
+ */
+export const typeLabels: Record<string, string> = {
+  local: 'Local CA',
+  local_ca: 'Local CA',       // backward compat (some frontend references)
+  acme: 'ACME',
+  stepca: 'step-ca',
+  openssl: 'OpenSSL/Custom',
+  VaultPKI: 'Vault PKI',
+  DigiCert: 'DigiCert',
+  manual: 'Manual',
+};
+
+/**
+ * All supported issuer types + 2 "Coming Soon" stubs.
+ * Order: most common first, coming-soon last.
+ */
+export const issuerTypes: IssuerTypeConfig[] = [
+  {
+    id: 'acme',
+    name: 'ACME',
+    description: "Let's Encrypt, ZeroSSL, or any ACME-compatible CA",
+    icon: '\uD83D\uDD12',
+    configFields: [
+      { key: 'directory_url', label: 'Directory URL', placeholder: 'https://acme-v02.api.letsencrypt.org/directory', required: true },
+      { key: 'email', label: 'Email', placeholder: 'admin@example.com', required: true },
+      { key: 'challenge_type', label: 'Challenge Type', type: 'select', options: ['http-01', 'dns-01', 'dns-persist-01'], required: false, defaultValue: 'http-01' },
+      { key: 'eab_kid', label: 'EAB Key ID', placeholder: 'External Account Binding Key ID (optional)', required: false },
+      { key: 'eab_hmac', label: 'EAB HMAC Key', placeholder: 'External Account Binding HMAC key', required: false, type: 'password', sensitive: true },
+    ],
+  },
+  {
+    id: 'local',
+    name: 'Local CA',
+    description: 'Self-signed or subordinate CA for internal certificates',
+    icon: '\uD83C\uDFE0',
+    configFields: [
+      { key: 'ca_cert_path', label: 'CA Cert Path (optional)', placeholder: '/path/to/ca.crt', required: false },
+      { key: 'ca_key_path', label: 'CA Key Path (optional)', placeholder: '/path/to/ca.key', required: false, sensitive: true },
+    ],
+  },
+  {
+    id: 'stepca',
+    name: 'step-ca',
+    description: 'Smallstep private CA with JWK provisioner auth',
+    icon: '\uD83D\uDC63',
+    configFields: [
+      { key: 'ca_url', label: 'CA URL', placeholder: 'https://ca.example.com', required: true },
+      { key: 'provisioner_name', label: 'Provisioner Name', placeholder: 'my-provisioner', required: true },
+      { key: 'provisioner_key', label: 'Provisioner Key (JWK)', placeholder: '{...}', type: 'textarea', required: true, sensitive: true },
+    ],
+  },
+  {
+    id: 'VaultPKI',
+    name: 'Vault PKI',
+    description: 'HashiCorp Vault PKI secrets engine',
+    icon: '\uD83D\uDD10',
+    configFields: [
+      { key: 'addr', label: 'Vault Address', placeholder: 'https://vault.internal:8200', required: true },
+      { key: 'token', label: 'Vault Token', placeholder: 'hvs.CAES...', required: true, type: 'password', sensitive: true },
+      { key: 'mount', label: 'PKI Mount Path', placeholder: 'pki', required: false, defaultValue: 'pki' },
+      { key: 'role', label: 'PKI Role Name', placeholder: 'web-certs', required: true },
+      { key: 'ttl', label: 'Certificate TTL', placeholder: '8760h', required: false, defaultValue: '8760h' },
+    ],
+  },
+  {
+    id: 'DigiCert',
+    name: 'DigiCert CertCentral',
+    description: 'DigiCert CertCentral for OV/EV certificates',
+    icon: '\uD83C\uDF10',
+    configFields: [
+      { key: 'api_key', label: 'DigiCert API Key', placeholder: 'Your DigiCert API key', required: true, type: 'password', sensitive: true },
+      { key: 'org_id', label: 'Organization ID', placeholder: '12345', required: true },
+      { key: 'product_type', label: 'Product Type', type: 'select', options: ['ssl_basic', 'ssl_plus', 'ssl_wildcard', 'ssl_ev_basic', 'ssl_ev_plus'], required: false, defaultValue: 'ssl_basic' },
+      { key: 'base_url', label: 'API Base URL Override', placeholder: 'https://www.digicert.com/services/v2', required: false },
+    ],
+  },
+  {
+    id: 'openssl',
+    name: 'OpenSSL/Custom',
+    description: 'Script-based signing with your own CA',
+    icon: '\uD83D\uDD27',
+    configFields: [
+      { key: 'sign_script', label: 'Sign Script Path', placeholder: '/path/to/sign.sh', required: true },
+      { key: 'revoke_script', label: 'Revoke Script Path (optional)', placeholder: '/path/to/revoke.sh', required: false },
+      { key: 'crl_script', label: 'CRL Script Path (optional)', placeholder: '/path/to/crl.sh', required: false },
+      { key: 'timeout_seconds', label: 'Timeout (seconds)', placeholder: '30', type: 'number', required: false },
+    ],
+  },
+  {
+    id: 'sectigo',
+    name: 'Sectigo',
+    description: 'Sectigo Certificate Manager \u2014 coming soon',
+    icon: '\uD83D\uDCE6',
+    configFields: [],
+    comingSoon: true,
+  },
+  {
+    id: 'entrust',
+    name: 'Entrust',
+    description: 'Entrust Certificate Services \u2014 coming soon',
+    icon: '\uD83D\uDCE6',
+    configFields: [],
+    comingSoon: true,
+  },
+];
+
+/** Sensitive config key patterns for redaction in display */
+const SENSITIVE_PATTERNS = ['password', 'secret', 'token', 'key', 'hmac', 'private'];
+
+/** Check if a config key should be redacted */
+export function isSensitiveKey(key: string): boolean {
+  const lower = key.toLowerCase();
+  return SENSITIVE_PATTERNS.some(p => lower.includes(p));
+}
+
+/** Redact sensitive values in a config object */
+export function redactConfig(config: Record<string, unknown>): Record<string, unknown> {
+  return Object.fromEntries(
+    Object.entries(config).map(([k, v]) => [k, isSensitiveKey(k) ? '********' : v])
+  );
+}
+
+/**
+ * Returns catalog status info per issuer type.
+ * M36 (Onboarding) will use this to detect first-run state.
+ */
+export function getIssuerCatalogStatus(
+  configuredIssuers: { type: string }[]
+): { type: IssuerTypeConfig; status: 'connected' | 'available' | 'coming_soon'; count: number }[] {
+  return issuerTypes.map(t => {
+    if (t.comingSoon) {
+      return { type: t, status: 'coming_soon' as const, count: 0 };
+    }
+    // Match both the canonical id and common aliases
+    const aliases: Record<string, string[]> = {
+      local: ['local', 'local_ca'],
+    };
+    const matchIds = aliases[t.id] || [t.id];
+    const matching = configuredIssuers.filter(i => matchIds.includes(i.type));
+    return {
+      type: t,
+      status: matching.length > 0 ? 'connected' as const : 'available' as const,
+      count: matching.length,
+    };
+  });
+}

web/src/pages/AgentFleetPage.tsx

@@ -13,6 +13,14 @@ const OS_COLORS: Record<string, string> = {
   unknown: '#64748b',
 };
 
+const OS_DISPLAY_NAMES: Record<string, string> = {
+  darwin: 'macOS',
+};
+
+function displayOS(os: string): string {
+  return OS_DISPLAY_NAMES[os.toLowerCase()] || os;
+}
+
 const STATUS_COLORS: Record<string, string> = {
   Online: '#10b981',
   Offline: '#ef4444',
@@ -86,7 +94,7 @@ export default function AgentFleetPage() {
     return acc;
   }, {});
   const osPieData = Object.entries(osDistribution).map(([name, value]) => ({
-    name,
+    name: displayOS(name),
     value,
     fill: OS_COLORS[name.toLowerCase()] || '#64748b',
   }));
@@ -216,7 +224,7 @@ export default function AgentFleetPage() {
                         style={{ backgroundColor: OS_COLORS[group.os.toLowerCase()] || '#64748b' }}
                       />
                       <h4 className="text-sm font-medium text-ink">
-                        {group.os} / {group.arch}
+                        {displayOS(group.os)} / {group.arch}
                       </h4>
                       <span className="text-xs text-ink-faint">
                         {group.agents.length} agent{group.agents.length !== 1 ? 's' : ''}

web/src/pages/CertificatesPage.tsx

@@ -1,7 +1,7 @@
 import { useState } from 'react';
 import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query';
 import { useNavigate } from 'react-router-dom';
-import { getCertificates, createCertificate, triggerRenewal, revokeCertificate, updateCertificate, getOwners } from '../api/client';
+import { getCertificates, createCertificate, triggerRenewal, revokeCertificate, updateCertificate, getOwners, getProfiles, getIssuers } from '../api/client';
 import { REVOCATION_REASONS } from '../api/types';
 import PageHeader from '../components/PageHeader';
 import DataTable from '../components/DataTable';
@@ -16,20 +16,66 @@ function CreateCertificateModal({ onClose, onSuccess }: { onClose: () => void; o
     name: '',
     id: '',
     common_name: '',
+    sans: '',
     environment: 'production',
     issuer_id: '',
+    certificate_profile_id: '',
     owner_id: '',
     team_id: '',
     renewal_policy_id: '',
+    tags: '',
   });
   const [error, setError] = useState('');
 
+  const { data: profilesResp } = useQuery({
+    queryKey: ['profiles'],
+    queryFn: () => getProfiles(),
+  });
+  const { data: issuersResp } = useQuery({
+    queryKey: ['issuers'],
+    queryFn: () => getIssuers(),
+  });
+  const profiles = profilesResp?.data || [];
+  const issuers = issuersResp?.data || [];
+
+  const selectedProfile = profiles.find(p => p.id === form.certificate_profile_id);
+  const ttlLabel = selectedProfile
+    ? selectedProfile.max_ttl_seconds < 3600
+      ? `${Math.round(selectedProfile.max_ttl_seconds / 60)}m`
+      : selectedProfile.max_ttl_seconds < 86400
+        ? `${Math.round(selectedProfile.max_ttl_seconds / 3600)}h`
+        : `${Math.round(selectedProfile.max_ttl_seconds / 86400)}d`
+    : null;
+
   const mutation = useMutation({
-    mutationFn: () => createCertificate(form),
+    mutationFn: () => {
+      const payload: Record<string, unknown> = { ...form };
+      // Convert comma-separated SANs to array
+      if (form.sans.trim()) {
+        payload.sans = form.sans.split(',').map(s => s.trim()).filter(Boolean);
+      } else {
+        delete payload.sans;
+      }
+      // Convert comma-separated key=value tags to object
+      if (form.tags.trim()) {
+        const tags: Record<string, string> = {};
+        form.tags.split(',').forEach(pair => {
+          const [k, ...v] = pair.split('=');
+          if (k?.trim()) tags[k.trim()] = v.join('=').trim();
+        });
+        payload.tags = tags;
+      } else {
+        delete payload.tags;
+      }
+      return createCertificate(payload);
+    },
     onSuccess: () => onSuccess(),
     onError: (err: Error) => setError(err.message),
   });
 
+  const inputClass = "w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20";
+  const selectClass = "w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink";
+
   return (
     <div className="fixed inset-0 bg-black/40 flex items-center justify-center z-50" onClick={onClose}>
       <div className="bg-surface border border-surface-border rounded p-6 w-full max-w-lg shadow-xl" onClick={e => e.stopPropagation()}>
@@ -39,57 +85,90 @@ function CreateCertificateModal({ onClose, onSuccess }: { onClose: () => void; o
           <div>
             <label className="text-xs text-ink-muted block mb-1">Name *</label>
             <input value={form.name} onChange={e => setForm(f => ({ ...f, name: e.target.value }))}
-              className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
+              className={inputClass}
               placeholder="API Production Cert" />
           </div>
           <div>
             <label className="text-xs text-ink-muted block mb-1">ID (optional)</label>
             <input value={form.id} onChange={e => setForm(f => ({ ...f, id: e.target.value }))}
-              className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
+              className={inputClass}
               placeholder="mc-api-prod (auto-generated if empty)" />
           </div>
           <div>
             <label className="text-xs text-ink-muted block mb-1">Common Name *</label>
             <input value={form.common_name} onChange={e => setForm(f => ({ ...f, common_name: e.target.value }))}
-              className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
+              className={inputClass}
               placeholder="api.example.com" />
           </div>
+          <div>
+            <label className="text-xs text-ink-muted block mb-1">SANs (comma-separated)</label>
+            <input value={form.sans} onChange={e => setForm(f => ({ ...f, sans: e.target.value }))}
+              className={inputClass}
+              placeholder="api.example.com, api-v2.example.com" />
+          </div>
+          <div className="grid grid-cols-2 gap-3">
+            <div>
+              <label className="text-xs text-ink-muted block mb-1">Issuer *</label>
+              <select value={form.issuer_id} onChange={e => setForm(f => ({ ...f, issuer_id: e.target.value }))}
+                className={selectClass}>
+                <option value="">Select issuer...</option>
+                {issuers.map(i => (
+                  <option key={i.id} value={i.id}>{i.name}</option>
+                ))}
+              </select>
+            </div>
+            <div>
+              <label className="text-xs text-ink-muted block mb-1">
+                Profile {ttlLabel && <span className="text-brand-400 font-medium">(TTL: {ttlLabel})</span>}
+              </label>
+              <select value={form.certificate_profile_id} onChange={e => setForm(f => ({ ...f, certificate_profile_id: e.target.value }))}
+                className={selectClass}>
+                <option value="">Select profile...</option>
+                {profiles.map(p => (
+                  <option key={p.id} value={p.id}>
+                    {p.name}{p.max_ttl_seconds ? ` (${p.max_ttl_seconds < 3600 ? `${Math.round(p.max_ttl_seconds / 60)}m` : p.max_ttl_seconds < 86400 ? `${Math.round(p.max_ttl_seconds / 3600)}h` : `${Math.round(p.max_ttl_seconds / 86400)}d`})` : ''}
+                  </option>
+                ))}
+              </select>
+            </div>
+          </div>
           <div className="grid grid-cols-2 gap-3">
             <div>
               <label className="text-xs text-ink-muted block mb-1">Environment</label>
               <select value={form.environment} onChange={e => setForm(f => ({ ...f, environment: e.target.value }))}
-                className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink">
+                className={selectClass}>
                 <option value="production">Production</option>
                 <option value="staging">Staging</option>
                 <option value="development">Development</option>
               </select>
             </div>
             <div>
-              <label className="text-xs text-ink-muted block mb-1">Issuer ID *</label>
-              <input value={form.issuer_id} onChange={e => setForm(f => ({ ...f, issuer_id: e.target.value }))}
-                className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
-                placeholder="iss-local" />
+              <label className="text-xs text-ink-muted block mb-1">Policy</label>
+              <input value={form.renewal_policy_id} onChange={e => setForm(f => ({ ...f, renewal_policy_id: e.target.value }))}
+                className={inputClass}
+                placeholder="rp-standard" />
             </div>
           </div>
-          <div className="grid grid-cols-3 gap-3">
+          <div className="grid grid-cols-2 gap-3">
             <div>
-              <label className="text-xs text-ink-muted block mb-1">Owner ID</label>
+              <label className="text-xs text-ink-muted block mb-1">Owner</label>
               <input value={form.owner_id} onChange={e => setForm(f => ({ ...f, owner_id: e.target.value }))}
-                className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
+                className={inputClass}
                 placeholder="o-alice" />
             </div>
             <div>
-              <label className="text-xs text-ink-muted block mb-1">Team ID</label>
+              <label className="text-xs text-ink-muted block mb-1">Team</label>
               <input value={form.team_id} onChange={e => setForm(f => ({ ...f, team_id: e.target.value }))}
-                className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
+                className={inputClass}
                 placeholder="t-platform" />
             </div>
-            <div>
-              <label className="text-xs text-ink-muted block mb-1">Policy ID</label>
-              <input value={form.renewal_policy_id} onChange={e => setForm(f => ({ ...f, renewal_policy_id: e.target.value }))}
-                className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400 focus:ring-1 focus:ring-brand-400/20"
-                placeholder="rp-standard" />
-            </div>
+          </div>
+          <div>
+            <label className="text-xs text-ink-muted block mb-1">Tags</label>
+            <input value={form.tags} onChange={e => setForm(f => ({ ...f, tags: e.target.value }))}
+              className={inputClass}
+              placeholder="env=prod, team=platform, app=api" />
+            <p className="text-xs text-ink-faint mt-0.5">Comma-separated key=value pairs</p>
           </div>
         </div>
         <div className="flex justify-end gap-3 mt-6">
@@ -245,15 +324,25 @@ export default function CertificatesPage() {
   const queryClient = useQueryClient();
   const [statusFilter, setStatusFilter] = useState('');
   const [envFilter, setEnvFilter] = useState('');
+  const [issuerFilter, setIssuerFilter] = useState('');
+  const [ownerFilter, setOwnerFilter] = useState('');
+  const [profileFilter, setProfileFilter] = useState('');
   const [showCreate, setShowCreate] = useState(false);
   const [selectedIds, setSelectedIds] = useState<Set<string>>(new Set());
   const [showBulkRevoke, setShowBulkRevoke] = useState(false);
   const [showBulkReassign, setShowBulkReassign] = useState(false);
   const [bulkRenewProgress, setBulkRenewProgress] = useState<{ done: number; total: number; running: boolean } | null>(null);
 
+  const { data: issuersData } = useQuery({ queryKey: ['issuers-filter'], queryFn: () => getIssuers({ per_page: '100' }) });
+  const { data: ownersData } = useQuery({ queryKey: ['owners-filter'], queryFn: () => getOwners({ per_page: '100' }) });
+  const { data: profilesData } = useQuery({ queryKey: ['profiles-filter'], queryFn: () => getProfiles({ per_page: '100' }) });
+
   const params: Record<string, string> = {};
   if (statusFilter) params.status = statusFilter;
   if (envFilter) params.environment = envFilter;
+  if (issuerFilter) params.issuer_id = issuerFilter;
+  if (ownerFilter) params.owner_id = ownerFilter;
+  if (profileFilter) params.profile_id = profileFilter;
 
   const { data, isLoading, error, refetch } = useQuery({
     queryKey: ['certificates', params],
@@ -302,7 +391,8 @@ export default function CertificatesPage() {
         );
       },
     },
-    { key: 'env', label: 'Environment', render: (c) => <span className="text-ink-muted">{c.environment || '—'}</span> },
+    { key: 'last_renewal', label: 'Last Renewal', render: (c) => <span className="text-xs text-ink-muted">{c.last_renewal_at ? formatDate(c.last_renewal_at) : '—'}</span> },
+    { key: 'last_deploy', label: 'Last Deploy', render: (c) => <span className="text-xs text-ink-muted">{c.last_deployment_at ? formatDate(c.last_deployment_at) : '—'}</span> },
     { key: 'issuer', label: 'Issuer', render: (c) => <span className="text-ink-muted text-xs">{c.issuer_id}</span> },
     { key: 'owner', label: 'Owner', render: (c) => <span className="text-ink-muted text-xs">{c.owner_id}</span> },
   ];
@@ -382,6 +472,36 @@ export default function CertificatesPage() {
           <option value="staging">Staging</option>
           <option value="development">Development</option>
         </select>
+        <select
+          value={issuerFilter}
+          onChange={e => setIssuerFilter(e.target.value)}
+          className="bg-white border border-surface-border rounded px-3 py-1.5 text-sm text-ink"
+        >
+          <option value="">All issuers</option>
+          {issuersData?.data?.map(i => (
+            <option key={i.id} value={i.id}>{i.name}</option>
+          ))}
+        </select>
+        <select
+          value={ownerFilter}
+          onChange={e => setOwnerFilter(e.target.value)}
+          className="bg-white border border-surface-border rounded px-3 py-1.5 text-sm text-ink"
+        >
+          <option value="">All owners</option>
+          {ownersData?.data?.map(o => (
+            <option key={o.id} value={o.id}>{o.name}</option>
+          ))}
+        </select>
+        <select
+          value={profileFilter}
+          onChange={e => setProfileFilter(e.target.value)}
+          className="bg-white border border-surface-border rounded px-3 py-1.5 text-sm text-ink"
+        >
+          <option value="">All profiles</option>
+          {profilesData?.data?.map(p => (
+            <option key={p.id} value={p.id}>{p.name}</option>
+          ))}
+        </select>
       </div>
       <div className="flex-1 overflow-y-auto">
         {error ? (

web/src/pages/DiscoveryPage.tsx

@@ -197,6 +197,18 @@ export default function DiscoveryPage() {
       label: 'Expiry',
       render: (c) => <span className="text-xs">{formatExpiry(c.not_after)}</span>,
     },
+    {
+      key: 'key_info',
+      label: 'Key',
+      render: (c) => (
+        <div className="flex items-center gap-1">
+          <span className="text-xs text-ink-muted">{c.key_algorithm}{c.key_size ? ` ${c.key_size}` : ''}</span>
+          {c.is_ca && (
+            <span className="text-[10px] px-1.5 py-0.5 rounded bg-purple-100 text-purple-700 font-medium">CA</span>
+          )}
+        </div>
+      ),
+    },
     {
       key: 'fingerprint',
       label: 'Fingerprint',

web/src/pages/IssuerDetailPage.tsx

@@ -1,4 +1,4 @@
-import { useParams } from 'react-router-dom';
+import { useParams, useNavigate } from 'react-router-dom';
 import { useQuery, useMutation } from '@tanstack/react-query';
 import { getIssuer, testIssuerConnection, getCertificates } from '../api/client';
 import PageHeader from '../components/PageHeader';
@@ -7,15 +7,8 @@ import DataTable from '../components/DataTable';
 import type { Column } from '../components/DataTable';
 import ErrorState from '../components/ErrorState';
 import { formatDateTime } from '../api/utils';
-import type { Certificate } from '../api/types';
-
-const typeLabels: Record<string, string> = {
-  local_ca: 'Local CA',
-  acme: 'ACME (Let\'s Encrypt)',
-  step_ca: 'step-ca',
-  openssl: 'OpenSSL / Custom',
-  vault: 'Vault PKI',
-};
+import type { Certificate, Issuer } from '../api/types';
+import { typeLabels, redactConfig } from '../config/issuerTypes';
 
 function InfoRow({ label, value }: { label: string; value: React.ReactNode }) {
   return (
@@ -26,8 +19,17 @@ function InfoRow({ label, value }: { label: string; value: React.ReactNode }) {
   );
 }
 
+/** Derive display status from backend enabled boolean */
+function issuerStatus(issuer: Issuer): string {
+  if (issuer.enabled !== undefined) {
+    return issuer.enabled ? 'Enabled' : 'Disabled';
+  }
+  return issuer.status || 'Unknown';
+}
+
 export default function IssuerDetailPage() {
   const { id } = useParams<{ id: string }>();
+  const navigate = useNavigate();
 
   const { data: issuer, isLoading, error, refetch } = useQuery({
     queryKey: ['issuer', id],
@@ -65,13 +67,7 @@ export default function IssuerDetailPage() {
     );
   }
 
-  // Redact sensitive config fields
-  const safeConfig = issuer.config ? Object.fromEntries(
-    Object.entries(issuer.config).map(([k, v]) => {
-      const sensitive = ['password', 'secret', 'token', 'key', 'hmac', 'private'].some(s => k.toLowerCase().includes(s));
-      return [k, sensitive ? '********' : v];
-    })
-  ) : {};
+  const safeConfig = issuer.config ? redactConfig(issuer.config) : {};
 
   const certColumns: Column<Certificate>[] = [
     {
@@ -94,13 +90,21 @@ export default function IssuerDetailPage() {
         title={issuer.name}
         subtitle={typeLabels[issuer.type] || issuer.type}
         action={
-          <button
-            onClick={() => testMutation.mutate()}
-            disabled={testMutation.isPending}
-            className="btn btn-primary text-xs disabled:opacity-50"
-          >
-            {testMutation.isPending ? 'Testing...' : 'Test Connection'}
-          </button>
+          <div className="flex gap-2">
+            <button
+              onClick={() => navigate(`/issuers?edit=${issuer.id}`)}
+              className="px-3 py-1.5 border border-surface-border rounded text-ink text-xs hover:bg-surface-hover transition-colors font-medium"
+            >
+              Edit
+            </button>
+            <button
+              onClick={() => testMutation.mutate()}
+              disabled={testMutation.isPending}
+              className="btn btn-primary text-xs disabled:opacity-50"
+            >
+              {testMutation.isPending ? 'Testing...' : 'Test Connection'}
+            </button>
+          </div>
         }
       />
 
@@ -123,7 +127,7 @@ export default function IssuerDetailPage() {
             <InfoRow label="ID" value={<span className="font-mono text-xs">{issuer.id}</span>} />
             <InfoRow label="Name" value={issuer.name} />
             <InfoRow label="Type" value={typeLabels[issuer.type] || issuer.type} />
-            <InfoRow label="Status" value={<StatusBadge status={issuer.status} />} />
+            <InfoRow label="Status" value={<StatusBadge status={issuerStatus(issuer)} />} />
             <InfoRow label="Created" value={formatDateTime(issuer.created_at)} />
           </div>
 

web/src/pages/IssuersPage.tsx

@@ -1,4 +1,4 @@
-import { useState } from 'react';
+import { useState, useMemo } from 'react';
 import { Link } from 'react-router-dom';
 import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query';
 import { getIssuers, testIssuerConnection, deleteIssuer, createIssuer } from '../api/client';
@@ -9,83 +9,27 @@ import StatusBadge from '../components/StatusBadge';
 import ErrorState from '../components/ErrorState';
 import { formatDateTime } from '../api/utils';
 import type { Issuer } from '../api/types';
+import { issuerTypes, typeLabels, getIssuerCatalogStatus, type IssuerTypeConfig } from '../config/issuerTypes';
+import TypeSelector from '../components/issuer/TypeSelector';
+import ConfigForm from '../components/issuer/ConfigForm';
+import ConfigDetailModal from '../components/issuer/ConfigDetailModal';
 
-const typeLabels: Record<string, string> = {
-  local_ca: 'Local CA',
-  acme: 'ACME',
-  stepca: 'step-ca',
-  openssl: 'OpenSSL/Custom',
-  vault: 'Vault PKI',
-  manual: 'Manual',
-};
-
-interface IssuerConfigField {
-  key: string;
-  label: string;
-  placeholder?: string;
-  required: boolean;
-  type?: string;
-  options?: string[];
-  defaultValue?: string;
+/** Derive display status from backend enabled boolean */
+function issuerStatus(issuer: Issuer): string {
+  if (issuer.enabled !== undefined) {
+    return issuer.enabled ? 'Enabled' : 'Disabled';
+  }
+  // Fallback for legacy data that may have status string
+  return issuer.status || 'Unknown';
 }
 
-interface IssuerTypeConfig {
-  id: string;
-  name: string;
-  description: string;
-  configFields: IssuerConfigField[];
-}
-
-const issuerTypes: IssuerTypeConfig[] = [
-  {
-    id: 'local_ca',
-    name: 'Local CA',
-    description: 'Self-signed or subordinate CA for certificate issuance',
-    configFields: [
-      { key: 'ca_cert_path', label: 'CA Cert Path (optional)', placeholder: '/path/to/ca.crt', required: false },
-      { key: 'ca_key_path', label: 'CA Key Path (optional)', placeholder: '/path/to/ca.key', required: false },
-    ],
-  },
-  {
-    id: 'acme',
-    name: 'ACME',
-    description: "Let's Encrypt or other ACME-compatible CA",
-    configFields: [
-      { key: 'directory_url', label: 'Directory URL', placeholder: 'https://acme-v02.api.letsencrypt.org/directory', required: true },
-      { key: 'email', label: 'Email', placeholder: 'admin@example.com', required: true },
-      { key: 'challenge_type', label: 'Challenge Type', type: 'select', options: ['http-01', 'dns-01', 'dns-persist-01'], required: false, defaultValue: 'http-01' },
-    ],
-  },
-  {
-    id: 'stepca',
-    name: 'step-ca',
-    description: 'Smallstep private CA',
-    configFields: [
-      { key: 'ca_url', label: 'CA URL', placeholder: 'https://ca.example.com', required: true },
-      { key: 'provisioner_name', label: 'Provisioner Name', placeholder: 'my-provisioner', required: true },
-      { key: 'provisioner_key', label: 'Provisioner Key (JWK)', placeholder: '{...}', type: 'textarea', required: true },
-    ],
-  },
-  {
-    id: 'openssl',
-    name: 'OpenSSL/Custom',
-    description: 'Script-based signing with your own CA',
-    configFields: [
-      { key: 'sign_script', label: 'Sign Script Path', placeholder: '/path/to/sign.sh', required: true },
-      { key: 'revoke_script', label: 'Revoke Script Path (optional)', placeholder: '/path/to/revoke.sh', required: false },
-      { key: 'crl_script', label: 'CRL Script Path (optional)', placeholder: '/path/to/crl.sh', required: false },
-      { key: 'timeout_seconds', label: 'Timeout (seconds)', placeholder: '30', type: 'number', required: false },
-    ],
-  },
-];
-
 export default function IssuersPage() {
   const queryClient = useQueryClient();
   const [testResult, setTestResult] = useState<{ id: string; ok: boolean; msg: string } | null>(null);
   const [showCreateModal, setShowCreateModal] = useState(false);
-  const [createStep, setCreateStep] = useState<'type' | 'config'>('type');
-  const [selectedType, setSelectedType] = useState<string | null>(null);
-  const [createForm, setCreateForm] = useState<Record<string, unknown>>({});
+  const [preselectedType, setPreselectedType] = useState<string | null>(null);
+  const [typeFilter, setTypeFilter] = useState<string>('');
+  const [configModal, setConfigModal] = useState<{ title: string; config: Record<string, unknown> } | null>(null);
 
   const { data, isLoading, error, refetch } = useQuery({
     queryKey: ['issuers'],
@@ -109,12 +53,22 @@ export default function IssuersPage() {
     onSuccess: () => {
       queryClient.invalidateQueries({ queryKey: ['issuers'] });
       setShowCreateModal(false);
-      setCreateStep('type');
-      setSelectedType(null);
-      setCreateForm({});
+      setPreselectedType(null);
     },
   });
 
+  const catalogStatus = useMemo(
+    () => getIssuerCatalogStatus(data?.data || []),
+    [data?.data]
+  );
+
+  // Filter issuers by type
+  const filteredIssuers = useMemo(() => {
+    if (!data?.data) return [];
+    if (!typeFilter) return data.data;
+    return data.data.filter(i => i.type === typeFilter);
+  }, [data?.data, typeFilter]);
+
   const columns: Column<Issuer>[] = [
     {
       key: 'name',
@@ -138,7 +92,7 @@ export default function IssuersPage() {
     {
       key: 'status',
       label: 'Status',
-      render: (i) => <StatusBadge status={i.status} />,
+      render: (i) => <StatusBadge status={issuerStatus(i)} />,
     },
     {
       key: 'config',
@@ -146,9 +100,15 @@ export default function IssuersPage() {
       render: (i) => {
         if (!i.config || Object.keys(i.config).length === 0) return <span className="text-ink-faint">&mdash;</span>;
         return (
-          <span className="text-xs text-ink-muted font-mono truncate max-w-xs block">
-            {JSON.stringify(i.config).slice(0, 60)}
-          </span>
+          <button
+            onClick={(e) => {
+              e.stopPropagation();
+              setConfigModal({ title: `${i.name} Configuration`, config: i.config });
+            }}
+            className="text-xs text-brand-400 hover:text-brand-500 transition-colors"
+          >
+            View Config
+          </button>
         );
       },
     },
@@ -184,14 +144,12 @@ export default function IssuersPage() {
     <>
       <PageHeader
         title="Issuers"
-        subtitle={data ? `${data.total} issuers` : undefined}
+        subtitle={data ? `${data.total} configured` : undefined}
         action={
           <button
             onClick={() => {
+              setPreselectedType(null);
               setShowCreateModal(true);
-              setCreateStep('type');
-              setSelectedType(null);
-              setCreateForm({});
             }}
             className="px-4 py-2 bg-brand-600 text-white rounded font-medium hover:bg-brand-700 transition-colors text-sm"
           >
@@ -205,49 +163,83 @@ export default function IssuersPage() {
           <button onClick={() => setTestResult(null)} className="ml-3 text-xs opacity-60 hover:opacity-100">dismiss</button>
         </div>
       )}
+
       <div className="flex-1 overflow-y-auto">
         {error ? (
           <ErrorState error={error as Error} onRetry={() => refetch()} />
         ) : (
-          <DataTable columns={columns} data={data?.data || []} isLoading={isLoading} emptyMessage="No issuers configured" />
+          <>
+            {/* Issuer Type Catalog Cards */}
+            <div className="px-6 py-4">
+              <h3 className="text-sm font-semibold text-ink-muted mb-3">Issuer Types</h3>
+              <div className="grid grid-cols-1 md:grid-cols-2 lg:grid-cols-3 xl:grid-cols-4 gap-3">
+                {catalogStatus.map(({ type, status, count }) => (
+                  <CatalogCard
+                    key={type.id}
+                    type={type}
+                    status={status}
+                    count={count}
+                    onConfigure={() => {
+                      setPreselectedType(type.id);
+                      setShowCreateModal(true);
+                    }}
+                    onFilter={() => {
+                      // Match both the canonical id and aliases
+                      const filterValue = type.id === 'local' ? 'local' : type.id;
+                      setTypeFilter(prev => prev === filterValue ? '' : filterValue);
+                    }}
+                  />
+                ))}
+              </div>
+            </div>
+
+            {/* Configured Issuers Table */}
+            <div className="px-6 pb-4">
+              <div className="flex items-center justify-between mb-3">
+                <h3 className="text-sm font-semibold text-ink-muted">Configured Issuers</h3>
+                <div className="flex items-center gap-2">
+                  <select
+                    value={typeFilter}
+                    onChange={(e) => setTypeFilter(e.target.value)}
+                    className="text-xs px-2 py-1.5 bg-surface border border-surface-border rounded text-ink focus:outline-none focus:border-brand-500"
+                  >
+                    <option value="">All Types</option>
+                    {issuerTypes.filter(t => !t.comingSoon).map(t => (
+                      <option key={t.id} value={t.id}>{t.name}</option>
+                    ))}
+                  </select>
+                </div>
+              </div>
+              <DataTable
+                columns={columns}
+                data={filteredIssuers}
+                isLoading={isLoading}
+                emptyMessage={typeFilter ? `No ${typeLabels[typeFilter] || typeFilter} issuers configured` : 'No issuers configured'}
+              />
+            </div>
+          </>
         )}
       </div>
 
+      {/* Config Detail Modal */}
+      {configModal && (
+        <ConfigDetailModal
+          title={configModal.title}
+          config={configModal.config}
+          onClose={() => setConfigModal(null)}
+        />
+      )}
+
+      {/* Create Issuer Modal */}
       {showCreateModal && (
         <CreateIssuerModal
-          step={createStep}
-          selectedType={selectedType}
-          form={createForm}
-          onTypeSelect={(type) => {
-            setSelectedType(type);
-            const typeConfig = issuerTypes.find((t) => t.id === type);
-            const defaultConfig: Record<string, unknown> = {};
-            if (typeConfig) {
-              typeConfig.configFields.forEach((field) => {
-                if (field.defaultValue) {
-                  defaultConfig[field.key] = field.defaultValue;
-                }
-              });
-            }
-            setCreateForm({ ...defaultConfig });
-            setCreateStep('config');
-          }}
-          onFormChange={(field, value) => {
-            setCreateForm({ ...createForm, [field]: value });
-          }}
-          onBack={() => setCreateStep('type')}
-          onSubmit={() => {
-            if (!selectedType || !createForm.name) return;
-            const config: Record<string, unknown> = { ...createForm };
-            const name = config.name as string;
-            delete config.name;
-            createMutation.mutate({ name, type: selectedType, config });
+          preselectedType={preselectedType}
+          onSubmit={(name, type, config) => {
+            createMutation.mutate({ name, type, config });
           }}
           onCancel={() => {
             setShowCreateModal(false);
-            setCreateStep('type');
-            setSelectedType(null);
-            setCreateForm({});
+            setPreselectedType(null);
           }}
           isSubmitting={createMutation.isPending}
         />
@@ -256,30 +248,94 @@ export default function IssuersPage() {
   );
 }
 
+// ─── Catalog Card ───────────────────────────────────────────────
+
+interface CatalogCardProps {
+  type: IssuerTypeConfig;
+  status: 'connected' | 'available' | 'coming_soon';
+  count: number;
+  onConfigure: () => void;
+  onFilter: () => void;
+}
+
+function CatalogCard({ type, status, count, onConfigure, onFilter }: CatalogCardProps) {
+  const statusConfig = {
+    connected: { label: `${count} configured`, cls: 'bg-emerald-500/10 text-emerald-400 border-emerald-500/30' },
+    available: { label: 'Available', cls: 'bg-brand-500/10 text-brand-400 border-brand-500/30' },
+    coming_soon: { label: 'Coming Soon', cls: 'bg-gray-500/10 text-gray-400 border-gray-500/30' },
+  };
+  const { label, cls } = statusConfig[status];
+
+  return (
+    <div className={`p-4 border rounded-lg ${status === 'coming_soon' ? 'border-surface-border/50 opacity-60' : 'border-surface-border'}`}>
+      <div className="flex items-start justify-between mb-2">
+        <div className="flex items-center gap-2">
+          <span className="text-lg">{type.icon}</span>
+          <span className="font-medium text-ink text-sm">{type.name}</span>
+        </div>
+        <span className={`text-xs px-2 py-0.5 rounded-full border ${cls}`}>{label}</span>
+      </div>
+      <p className="text-xs text-ink-muted mb-3">{type.description}</p>
+      {status === 'connected' && (
+        <button
+          onClick={onFilter}
+          className="text-xs text-brand-400 hover:text-brand-500 transition-colors"
+        >
+          View issuers
+        </button>
+      )}
+      {status === 'available' && (
+        <button
+          onClick={onConfigure}
+          className="text-xs px-3 py-1 bg-brand-600 text-white rounded hover:bg-brand-700 transition-colors"
+        >
+          Configure
+        </button>
+      )}
+    </div>
+  );
+}
+
+// ─── Create Issuer Modal ────────────────────────────────────────
+
 interface CreateIssuerModalProps {
-  step: 'type' | 'config';
-  selectedType: string | null;
-  form: Record<string, unknown>;
-  onTypeSelect: (type: string) => void;
-  onFormChange: (field: string, value: unknown) => void;
-  onBack: () => void;
-  onSubmit: () => void;
+  preselectedType: string | null;
+  onSubmit: (name: string, type: string, config: Record<string, unknown>) => void;
   onCancel: () => void;
   isSubmitting: boolean;
 }
 
-function CreateIssuerModal({
-  step,
-  selectedType,
-  form,
-  onTypeSelect,
-  onFormChange,
-  onBack,
-  onSubmit,
-  onCancel,
-  isSubmitting,
-}: CreateIssuerModalProps) {
-  const selectedTypeConfig = issuerTypes.find((t) => t.id === selectedType);
+function CreateIssuerModal({ preselectedType, onSubmit, onCancel, isSubmitting }: CreateIssuerModalProps) {
+  const [step, setStep] = useState<'type' | 'config'>(preselectedType ? 'config' : 'type');
+  const [selectedType, setSelectedType] = useState<string | null>(preselectedType);
+  const [form, setForm] = useState<Record<string, unknown>>(() => {
+    if (preselectedType) {
+      const tc = issuerTypes.find(t => t.id === preselectedType);
+      const defaults: Record<string, unknown> = {};
+      tc?.configFields.forEach(f => { if (f.defaultValue) defaults[f.key] = f.defaultValue; });
+      return defaults;
+    }
+    return {};
+  });
+
+  const selectedTypeConfig = issuerTypes.find(t => t.id === selectedType);
+
+  function handleTypeSelect(typeId: string) {
+    setSelectedType(typeId);
+    const tc = issuerTypes.find(t => t.id === typeId);
+    const defaults: Record<string, unknown> = {};
+    tc?.configFields.forEach(f => { if (f.defaultValue) defaults[f.key] = f.defaultValue; });
+    setForm(defaults);
+    setStep('config');
+  }
+
+  function handleSubmit() {
+    if (!selectedType || !form.name) return;
+    const config = { ...form };
+    const name = config.name as string;
+    delete config.name;
+    onSubmit(name, selectedType, config);
+  }
 
   return (
     <div className="fixed inset-0 bg-black bg-opacity-50 z-50 flex items-center justify-center">
@@ -289,10 +345,7 @@ function CreateIssuerModal({
           <h2 className="text-lg font-semibold text-ink">
             {step === 'type' ? 'Create Issuer' : `Configure ${selectedTypeConfig?.name || 'Issuer'}`}
           </h2>
-          <button
-            onClick={onCancel}
-            className="text-ink-muted hover:text-ink transition-colors"
-          >
+          <button onClick={onCancel} className="text-ink-muted hover:text-ink transition-colors">
             ✕
           </button>
         </div>
@@ -300,79 +353,28 @@ function CreateIssuerModal({
         {/* Content */}
         <div className="px-6 py-6">
           {step === 'type' ? (
-            <div className="grid grid-cols-2 gap-4">
-              {issuerTypes.map((type) => (
-                <button
-                  key={type.id}
-                  onClick={() => onTypeSelect(type.id)}
-                  className="p-4 border border-surface-border rounded-lg hover:border-brand-500 hover:bg-opacity-5 transition-all text-left"
-                >
-                  <div className="font-medium text-ink">{type.name}</div>
-                  <div className="text-sm text-ink-muted mt-1">{type.description}</div>
-                </button>
-              ))}
-            </div>
+            <TypeSelector onSelect={handleTypeSelect} />
           ) : (
             <div className="space-y-5">
-              {/* Name field always shown */}
+              {/* Name field */}
               <div>
                 <label className="block text-sm font-medium text-ink mb-2">Issuer Name *</label>
                 <input
                   type="text"
                   value={(form.name as string) || ''}
-                  onChange={(e) => onFormChange('name', e.target.value)}
+                  onChange={(e) => setForm({ ...form, name: e.target.value })}
                   placeholder="e.g., Production CA"
                   className="w-full px-3 py-2 bg-surface border border-surface-border rounded text-ink placeholder-ink-faint focus:outline-none focus:border-brand-500 transition-colors"
                 />
               </div>
-
-              {/* Type-specific fields */}
-              {selectedTypeConfig?.configFields.map((field) => (
-                <div key={field.key}>
-                  <label className="block text-sm font-medium text-ink mb-2">
-                    {field.label}
-                    {field.required && <span className="text-red-600 ml-1">*</span>}
-                  </label>
-                  {field.type === 'select' ? (
-                    <select
-                      value={(form[field.key] as string) || ''}
-                      onChange={(e) => onFormChange(field.key, e.target.value)}
-                      className="w-full px-3 py-2 bg-surface border border-surface-border rounded text-ink focus:outline-none focus:border-brand-500 transition-colors"
-                    >
-                      <option value="">Select {field.label}</option>
-                      {field.options?.map((opt) => (
-                        <option key={opt} value={opt}>
-                          {opt}
-                        </option>
-                      ))}
-                    </select>
-                  ) : field.type === 'textarea' ? (
-                    <textarea
-                      value={(form[field.key] as string) || ''}
-                      onChange={(e) => onFormChange(field.key, e.target.value)}
-                      placeholder={field.placeholder}
-                      rows={4}
-                      className="w-full px-3 py-2 bg-surface border border-surface-border rounded text-ink placeholder-ink-faint focus:outline-none focus:border-brand-500 transition-colors font-mono text-xs"
-                    />
-                  ) : field.type === 'number' ? (
-                    <input
-                      type="number"
-                      value={(form[field.key] as number | string) || ''}
-                      onChange={(e) => onFormChange(field.key, e.target.value ? parseInt(e.target.value, 10) : '')}
-                      placeholder={field.placeholder}
-                      className="w-full px-3 py-2 bg-surface border border-surface-border rounded text-ink placeholder-ink-faint focus:outline-none focus:border-brand-500 transition-colors"
-                    />
-                  ) : (
-                    <input
-                      type="text"
-                      value={(form[field.key] as string) || ''}
-                      onChange={(e) => onFormChange(field.key, e.target.value)}
-                      placeholder={field.placeholder}
-                      className="w-full px-3 py-2 bg-surface border border-surface-border rounded text-ink placeholder-ink-faint focus:outline-none focus:border-brand-500 transition-colors"
-                    />
-                  )}
-                </div>
-              ))}
+              {/* Type-specific fields via ConfigForm */}
+              {selectedTypeConfig && (
+                <ConfigForm
+                  fields={selectedTypeConfig.configFields}
+                  values={form}
+                  onChange={(key, value) => setForm({ ...form, [key]: value })}
+                />
+              )}
             </div>
           )}
         </div>
@@ -381,7 +383,7 @@ function CreateIssuerModal({
         <div className="border-t border-surface-border px-6 py-4 flex justify-end gap-3">
           {step === 'config' && (
             <button
-              onClick={onBack}
+              onClick={() => setStep('type')}
               className="px-4 py-2 border border-surface-border rounded text-ink hover:bg-surface-hover transition-colors text-sm font-medium"
             >
               Back
@@ -395,22 +397,13 @@ function CreateIssuerModal({
           </button>
           {step === 'config' && (
             <button
-              onClick={onSubmit}
+              onClick={handleSubmit}
               disabled={isSubmitting || !form.name}
               className="px-4 py-2 bg-brand-600 text-white rounded text-sm font-medium hover:bg-brand-700 transition-colors disabled:opacity-50 disabled:cursor-not-allowed"
             >
               {isSubmitting ? 'Creating...' : 'Create Issuer'}
             </button>
           )}
-          {step === 'type' && (
-            <button
-              onClick={() => selectedType && onTypeSelect(selectedType)}
-              disabled={!selectedType}
-              className="px-4 py-2 bg-brand-600 text-white rounded text-sm font-medium hover:bg-brand-700 transition-colors disabled:opacity-50 disabled:cursor-not-allowed"
-            >
-              Next
-            </button>
-          )}
         </div>
       </div>
     </div>

web/src/pages/JobsPage.tsx

@@ -136,6 +136,15 @@ export default function JobsPage() {
       label: 'Attempts',
       render: (j) => <span className="text-ink-muted">{j.attempts}/{j.max_attempts}</span>,
     },
+    {
+      key: 'error',
+      label: 'Error',
+      render: (j) => j.status === 'Failed' && j.error_message ? (
+        <span className="text-xs text-red-600 truncate max-w-[200px] inline-block" title={j.error_message}>
+          {j.error_message.length > 80 ? j.error_message.substring(0, 80) + '...' : j.error_message}
+        </span>
+      ) : <span className="text-xs text-ink-faint">—</span>,
+    },
     { key: 'scheduled', label: 'Scheduled', render: (j) => <span className="text-xs text-ink-muted">{formatDateTime(j.scheduled_at)}</span> },
     { key: 'completed', label: 'Completed', render: (j) => <span className="text-xs text-ink-muted">{formatDateTime(j.completed_at)}</span> },
     {

web/src/pages/ProfilesPage.tsx

@@ -25,11 +25,63 @@ interface CreateProfileModalProps {
   error: string | null;
 }
 
+const AVAILABLE_ALGORITHMS = ['RSA', 'ECDSA', 'Ed25519'];
+const ALGORITHM_MIN_SIZES: Record<string, number[]> = {
+  RSA: [2048, 3072, 4096],
+  ECDSA: [256, 384],
+  Ed25519: [0],
+};
+
+const AVAILABLE_EKUS = [
+  { value: 'serverAuth', label: 'Server Authentication (TLS)' },
+  { value: 'clientAuth', label: 'Client Authentication' },
+  { value: 'codeSigning', label: 'Code Signing' },
+  { value: 'emailProtection', label: 'Email Protection (S/MIME)' },
+  { value: 'timeStamping', label: 'Time Stamping' },
+];
+
+interface KeyAlgorithmEntry {
+  algorithm: string;
+  min_size: number;
+}
+
 function CreateProfileModal({ isOpen, onClose, onSuccess, isLoading, error }: CreateProfileModalProps) {
   const [name, setName] = useState('');
   const [description, setDescription] = useState('');
   const [ttl, setTtl] = useState('86400');
   const [shortLived, setShortLived] = useState(false);
+  const [keyAlgorithms, setKeyAlgorithms] = useState<KeyAlgorithmEntry[]>([
+    { algorithm: 'ECDSA', min_size: 256 },
+    { algorithm: 'RSA', min_size: 2048 },
+  ]);
+  const [selectedEkus, setSelectedEkus] = useState<string[]>(['serverAuth']);
+  const [sanPatterns, setSanPatterns] = useState('');
+  const [spiffePattern, setSpiffePattern] = useState('');
+
+  const addAlgorithm = () => {
+    const unused = AVAILABLE_ALGORITHMS.find(a => !keyAlgorithms.some(ka => ka.algorithm === a));
+    if (unused) {
+      setKeyAlgorithms([...keyAlgorithms, { algorithm: unused, min_size: ALGORITHM_MIN_SIZES[unused][0] }]);
+    }
+  };
+
+  const removeAlgorithm = (idx: number) => {
+    setKeyAlgorithms(keyAlgorithms.filter((_, i) => i !== idx));
+  };
+
+  const updateAlgorithm = (idx: number, field: 'algorithm' | 'min_size', value: string | number) => {
+    const updated = [...keyAlgorithms];
+    if (field === 'algorithm') {
+      updated[idx] = { algorithm: value as string, min_size: ALGORITHM_MIN_SIZES[value as string]?.[0] || 0 };
+    } else {
+      updated[idx] = { ...updated[idx], min_size: value as number };
+    }
+    setKeyAlgorithms(updated);
+  };
+
+  const toggleEku = (eku: string) => {
+    setSelectedEkus(prev => prev.includes(eku) ? prev.filter(e => e !== eku) : [...prev, eku]);
+  };
 
   const handleSubmit = async (e: React.FormEvent) => {
     e.preventDefault();
@@ -39,20 +91,31 @@ function CreateProfileModal({ isOpen, onClose, onSuccess, isLoading, error }: Cr
       description: description.trim(),
       max_ttl_seconds: parseInt(ttl) || 86400,
       allow_short_lived: shortLived,
+      allowed_key_algorithms: keyAlgorithms,
+      allowed_ekus: selectedEkus,
+      required_san_patterns: sanPatterns.trim() ? sanPatterns.split(',').map(s => s.trim()).filter(Boolean) : [],
+      spiffe_uri_pattern: spiffePattern.trim() || '',
       enabled: true,
     });
     setName('');
     setDescription('');
     setTtl('86400');
     setShortLived(false);
+    setKeyAlgorithms([{ algorithm: 'ECDSA', min_size: 256 }, { algorithm: 'RSA', min_size: 2048 }]);
+    setSelectedEkus(['serverAuth']);
+    setSanPatterns('');
+    setSpiffePattern('');
     onSuccess();
   };
 
   if (!isOpen) return null;
 
+  const inputClass = 'w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400';
+  const selectClass = 'bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400';
+
   return (
     <div className="fixed inset-0 bg-black/40 flex items-center justify-center z-50" onClick={onClose}>
-      <div className="bg-surface border border-surface-border rounded p-5 w-full max-w-md shadow-xl" onClick={e => e.stopPropagation()}>
+      <div className="bg-surface border border-surface-border rounded p-5 w-full max-w-lg shadow-xl max-h-[90vh] overflow-y-auto" onClick={e => e.stopPropagation()}>
         <h2 className="text-lg font-semibold text-ink mb-4">Create Profile</h2>
         {error && <div className="mb-4 p-3 bg-red-50 border border-red-200 rounded text-sm text-red-700">{error}</div>}
         <form onSubmit={handleSubmit} className="space-y-4">
@@ -61,7 +124,7 @@ function CreateProfileModal({ isOpen, onClose, onSuccess, isLoading, error }: Cr
             <input
               value={name}
               onChange={e => setName(e.target.value)}
-              className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400"
+              className={inputClass}
               placeholder="e.g., Web Server Certs"
               required
             />
@@ -71,7 +134,7 @@ function CreateProfileModal({ isOpen, onClose, onSuccess, isLoading, error }: Cr
             <textarea
               value={description}
               onChange={e => setDescription(e.target.value)}
-              className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400"
+              className={inputClass}
               placeholder="Optional description"
               rows={2}
             />
@@ -82,7 +145,7 @@ function CreateProfileModal({ isOpen, onClose, onSuccess, isLoading, error }: Cr
               type="number"
               value={ttl}
               onChange={e => setTtl(e.target.value)}
-              className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400"
+              className={inputClass}
               placeholder="86400"
             />
             <p className="text-xs text-ink-muted mt-1">
@@ -109,6 +172,97 @@ function CreateProfileModal({ isOpen, onClose, onSuccess, isLoading, error }: Cr
             />
             <label htmlFor="shortLived" className="text-sm text-ink">Allow short-lived certs</label>
           </div>
+
+          {/* Allowed Key Algorithms */}
+          <div>
+            <div className="flex items-center justify-between mb-1">
+              <label className="block text-sm font-medium text-ink">Allowed Key Algorithms</label>
+              {keyAlgorithms.length < AVAILABLE_ALGORITHMS.length && (
+                <button type="button" onClick={addAlgorithm} className="text-xs text-brand-600 hover:text-brand-700 font-medium">
+                  + Add
+                </button>
+              )}
+            </div>
+            <div className="space-y-2">
+              {keyAlgorithms.map((ka, idx) => (
+                <div key={idx} className="flex items-center gap-2">
+                  <select
+                    value={ka.algorithm}
+                    onChange={e => updateAlgorithm(idx, 'algorithm', e.target.value)}
+                    className={selectClass + ' flex-1'}
+                  >
+                    {AVAILABLE_ALGORITHMS.map(a => (
+                      <option key={a} value={a} disabled={a !== ka.algorithm && keyAlgorithms.some(k => k.algorithm === a)}>
+                        {a}
+                      </option>
+                    ))}
+                  </select>
+                  {ka.algorithm !== 'Ed25519' ? (
+                    <select
+                      value={ka.min_size}
+                      onChange={e => updateAlgorithm(idx, 'min_size', parseInt(e.target.value))}
+                      className={selectClass + ' w-24'}
+                    >
+                      {(ALGORITHM_MIN_SIZES[ka.algorithm] || []).map(s => (
+                        <option key={s} value={s}>{s}+</option>
+                      ))}
+                    </select>
+                  ) : (
+                    <span className="text-xs text-ink-muted w-24 text-center">fixed</span>
+                  )}
+                  <button type="button" onClick={() => removeAlgorithm(idx)} className="text-xs text-red-500 hover:text-red-600">
+                    Remove
+                  </button>
+                </div>
+              ))}
+              {keyAlgorithms.length === 0 && (
+                <p className="text-xs text-ink-faint">No algorithms configured. Click + Add to allow key types.</p>
+              )}
+            </div>
+          </div>
+
+          {/* Allowed EKUs */}
+          <div>
+            <label className="block text-sm font-medium text-ink mb-1">Allowed Extended Key Usages</label>
+            <div className="space-y-1.5">
+              {AVAILABLE_EKUS.map(eku => (
+                <label key={eku.value} className="flex items-center gap-2 cursor-pointer">
+                  <input
+                    type="checkbox"
+                    checked={selectedEkus.includes(eku.value)}
+                    onChange={() => toggleEku(eku.value)}
+                    className="w-4 h-4"
+                  />
+                  <span className="text-sm text-ink">{eku.label}</span>
+                </label>
+              ))}
+            </div>
+          </div>
+
+          {/* Required SAN Patterns */}
+          <div>
+            <label className="block text-sm font-medium text-ink mb-1">Required SAN Patterns</label>
+            <input
+              value={sanPatterns}
+              onChange={e => setSanPatterns(e.target.value)}
+              className={inputClass}
+              placeholder="e.g., *.example.com, api.internal"
+            />
+            <p className="text-xs text-ink-muted mt-1">Comma-separated patterns. Leave empty for no constraints.</p>
+          </div>
+
+          {/* SPIFFE URI Pattern */}
+          <div>
+            <label className="block text-sm font-medium text-ink mb-1">SPIFFE URI Pattern</label>
+            <input
+              value={spiffePattern}
+              onChange={e => setSpiffePattern(e.target.value)}
+              className={inputClass}
+              placeholder="e.g., spiffe://example.org/service/*"
+            />
+            <p className="text-xs text-ink-muted mt-1">Optional workload identity URI SAN pattern.</p>
+          </div>
+
           <div className="flex gap-2 pt-4">
             <button
               type="submit"

web/src/pages/TargetDetailPage.tsx

@@ -1,6 +1,7 @@
+import { useState } from 'react';
 import { useParams, Link } from 'react-router-dom';
-import { useQuery } from '@tanstack/react-query';
-import { getTarget, getJobs } from '../api/client';
+import { useQuery, useMutation, useQueryClient } from '@tanstack/react-query';
+import { getTarget, getJobs, updateTarget } from '../api/client';
 import PageHeader from '../components/PageHeader';
 import StatusBadge from '../components/StatusBadge';
 import DataTable from '../components/DataTable';
@@ -30,6 +31,18 @@ function InfoRow({ label, value }: { label: string; value: React.ReactNode }) {
 
 export default function TargetDetailPage() {
   const { id } = useParams<{ id: string }>();
+  const queryClient = useQueryClient();
+  const [isEditing, setIsEditing] = useState(false);
+  const [editName, setEditName] = useState('');
+  const [editHostname, setEditHostname] = useState('');
+
+  const updateMutation = useMutation({
+    mutationFn: (data: Partial<{ name: string; hostname: string }>) => updateTarget(id!, data),
+    onSuccess: () => {
+      queryClient.invalidateQueries({ queryKey: ['target', id] });
+      setIsEditing(false);
+    },
+  });
 
   const { data: target, isLoading, error, refetch } = useQuery({
     queryKey: ['target', id],
@@ -112,6 +125,18 @@ export default function TargetDetailPage() {
       <PageHeader
         title={target.name}
         subtitle={typeLabels[target.type] || target.type}
+        action={
+          <button
+            onClick={() => {
+              setEditName(target.name);
+              setEditHostname(target.hostname || '');
+              setIsEditing(true);
+            }}
+            className="px-3 py-1.5 border border-surface-border rounded text-ink text-xs hover:bg-surface-hover transition-colors font-medium"
+          >
+            Edit
+          </button>
+        }
       />
 
       <div className="flex-1 overflow-y-auto px-6 py-4 space-y-6">
@@ -139,11 +164,16 @@ export default function TargetDetailPage() {
             <h3 className="text-sm font-semibold text-ink-muted mb-4">Configuration</h3>
             {target.config && Object.keys(target.config).length > 0 ? (
               <div className="space-y-0">
-                {Object.entries(target.config).map(([key, val]) => (
-                  <InfoRow key={key} label={key.replace(/_/g, ' ')} value={
-                    <span className="font-mono text-xs truncate max-w-xs inline-block">{String(val)}</span>
-                  } />
-                ))}
+                {Object.entries(target.config).map(([key, val]) => {
+                  const sensitiveKeys = ['password', 'secret', 'token', 'key', 'winrm_password'];
+                  const isSensitive = sensitiveKeys.some(s => key.toLowerCase().includes(s));
+                  const displayVal = isSensitive && val ? '********' : String(val);
+                  return (
+                    <InfoRow key={key} label={key.replace(/_/g, ' ')} value={
+                      <span className="font-mono text-xs truncate max-w-xs inline-block">{displayVal}</span>
+                    } />
+                  );
+                })}
               </div>
             ) : (
               <div className="text-sm text-ink-faint py-4 text-center">No configuration data</div>
@@ -164,6 +194,36 @@ export default function TargetDetailPage() {
           />
         </div>
       </div>
+
+      {/* Edit Modal */}
+      {isEditing && (
+        <div className="fixed inset-0 bg-black/40 flex items-center justify-center z-50" onClick={() => setIsEditing(false)}>
+          <div className="bg-surface border border-surface-border rounded p-5 w-full max-w-md shadow-xl" onClick={e => e.stopPropagation()}>
+            <h2 className="text-lg font-semibold text-ink mb-4">Edit Target</h2>
+            {updateMutation.isError && (
+              <div className="mb-4 p-3 bg-red-50 border border-red-200 rounded text-sm text-red-700">
+                {(updateMutation.error as Error).message}
+              </div>
+            )}
+            <form onSubmit={e => { e.preventDefault(); updateMutation.mutate({ name: editName, hostname: editHostname }); }} className="space-y-4">
+              <div>
+                <label className="block text-sm font-medium text-ink mb-1">Name</label>
+                <input value={editName} onChange={e => setEditName(e.target.value)} className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400" />
+              </div>
+              <div>
+                <label className="block text-sm font-medium text-ink mb-1">Hostname</label>
+                <input value={editHostname} onChange={e => setEditHostname(e.target.value)} className="w-full bg-white border border-surface-border rounded px-3 py-2 text-sm text-ink focus:outline-none focus:border-brand-400" />
+              </div>
+              <div className="flex gap-2 pt-2">
+                <button type="submit" disabled={updateMutation.isPending} className="flex-1 btn btn-primary disabled:opacity-50">
+                  {updateMutation.isPending ? 'Saving...' : 'Save'}
+                </button>
+                <button type="button" onClick={() => setIsEditing(false)} className="flex-1 btn btn-ghost">Cancel</button>
+              </div>
+            </form>
+          </div>
+        </div>
+      )}
     </>
   );
 }

web/src/pages/TargetsPage.tsx

@@ -16,6 +16,7 @@ const typeLabels: Record<string, string> = {
   haproxy: 'HAProxy',
   traefik: 'Traefik',
   caddy: 'Caddy',
+  envoy: 'Envoy',
   f5_bigip: 'F5 BIG-IP',
   iis: 'IIS',
 };
@@ -26,8 +27,9 @@ const TARGET_TYPES = [
   { value: 'haproxy', label: 'HAProxy', description: 'Combined PEM file (cert+chain+key), optional validate, reload' },
   { value: 'traefik', label: 'Traefik', description: 'File provider deployment — writes cert/key to watched directory, auto-reload' },
   { value: 'caddy', label: 'Caddy', description: 'Admin API hot-reload or file-based deployment with configurable mode' },
+  { value: 'envoy', label: 'Envoy', description: 'File-based deployment — writes cert/key to watched directory. Optional SDS file generation.' },
   { value: 'f5_bigip', label: 'F5 BIG-IP', description: 'iControl REST via proxy agent (V3 implementation)' },
-  { value: 'iis', label: 'IIS', description: 'Windows IIS via agent-local PowerShell or proxy WinRM (V3 implementation)' },
+  { value: 'iis', label: 'IIS', description: 'Windows IIS via agent-local PowerShell or remote WinRM proxy agent' },
 ];
 
 const CONFIG_FIELDS: Record<string, { key: string; label: string; placeholder: string; required?: boolean }[]> = {
@@ -60,6 +62,13 @@ const CONFIG_FIELDS: Record<string, { key: string; label: string; placeholder: s
     { key: 'cert_file', label: 'Certificate Filename', placeholder: 'cert.pem (default)' },
     { key: 'key_file', label: 'Key Filename', placeholder: 'key.pem (default)' },
   ],
+  envoy: [
+    { key: 'cert_dir', label: 'Certificate Directory', placeholder: '/etc/envoy/certs', required: true },
+    { key: 'cert_filename', label: 'Certificate Filename', placeholder: 'cert.pem (default)' },
+    { key: 'key_filename', label: 'Key Filename', placeholder: 'key.pem (default)' },
+    { key: 'chain_filename', label: 'Chain Filename (optional)', placeholder: 'chain.pem (leave empty to append to cert)' },
+    { key: 'sds_config', label: 'Generate SDS Config', placeholder: 'true or false' },
+  ],
   f5_bigip: [
     { key: 'management_ip', label: 'Management IP', placeholder: '192.168.1.100', required: true },
     { key: 'partition', label: 'Partition', placeholder: 'Common' },
@@ -67,9 +76,18 @@ const CONFIG_FIELDS: Record<string, { key: string; label: string; placeholder: s
   ],
   iis: [
     { key: 'site_name', label: 'IIS Site Name', placeholder: 'Default Web Site', required: true },
-    { key: 'binding_ip', label: 'Binding IP', placeholder: '*' },
-    { key: 'binding_port', label: 'Binding Port', placeholder: '443' },
-    { key: 'cert_store', label: 'Certificate Store', placeholder: 'My' },
+    { key: 'cert_store', label: 'Certificate Store', placeholder: 'My', required: true },
+    { key: 'port', label: 'HTTPS Port', placeholder: '443' },
+    { key: 'ip_address', label: 'Binding IP', placeholder: '*' },
+    { key: 'binding_info', label: 'Host Header (SNI)', placeholder: 'www.example.com' },
+    { key: 'sni', label: 'Enable SNI', placeholder: 'true or false' },
+    { key: 'mode', label: 'Deployment Mode', placeholder: 'local (default) or winrm' },
+    { key: 'winrm.winrm_host', label: 'WinRM Host (remote mode)', placeholder: 'iis-server.example.com' },
+    { key: 'winrm.winrm_port', label: 'WinRM Port', placeholder: '5985 (HTTP) or 5986 (HTTPS)' },
+    { key: 'winrm.winrm_username', label: 'WinRM Username', placeholder: 'Administrator' },
+    { key: 'winrm.winrm_password', label: 'WinRM Password', placeholder: '(sensitive)' },
+    { key: 'winrm.winrm_https', label: 'WinRM Use HTTPS', placeholder: 'true or false' },
+    { key: 'winrm.winrm_insecure', label: 'WinRM Skip TLS Verify', placeholder: 'false' },
   ],
 };