Files
certctl/docs/operator/oidc-runbooks/google-workspace.md
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shankar0123 2893f9b48e auth-bundle-2 Phase 11: 6 per-IdP OIDC runbooks + index + docs/README wiring
Closes Phase 11 of cowork/auth-bundle-2-prompt.md. Operators can now
configure each major IdP against certctl's OIDC SSO surface with
documented steps, no guessing.

Files
=====

docs/operator/oidc-runbooks/index.md (NEW):
* Index page linking all six per-IdP runbooks.
* Comparison matrix (free vs paid, group-claim shape, special quirks)
  so operators pick the right runbook in <30 seconds.
* "Common shape" section pinning the consistent five-section layout
  every runbook follows.
* "Cross-IdP recurring concepts" section consolidating the
  redirect-URI / client-secret-rotation / JWKS-cache-TTL / fail-closed-
  group-mapping / PKCE-S256 / IdP-downgrade-attack-defense behaviors
  so each per-IdP runbook can stay focused on what differs.

docs/operator/oidc-runbooks/keycloak.md (NEW):
* Canonical reference. Mirrors the testfixtures/keycloak-realm.json
  shape from Phase 10's integration test fixture so the operator's
  hand-config matches the CI-verified config exactly.
* Step-by-step IdP-side: realm → client → groups → group-mapper →
  user. Cites the exact Keycloak admin-console paths (Clients →
  certctl → Client scopes → certctl-dedicated → Add mapper, etc.).
* GUI + API + MCP equivalents for the certctl-side configuration.
* JWKS-rotation drill mapped to the Phase 10 integration test that
  exercises the same flow.
* 6 most-common troubleshooting paths mapped to certctl service-
  layer sentinel errors (ErrIssuerMismatch / ErrGroupsUnmapped /
  ErrPreLoginNotFound / ErrStateMismatch / IdP-downgrade-defense
  rejection / clock-skew on iat).

docs/operator/oidc-runbooks/authentik.md (NEW):
* Authentik-specific deltas vs Keycloak: provider/application split,
  property-mapping abstraction, explicit `groups` scope requirement,
  hashed-vs-email subject mode, signing-key rotation via Crypto/Tokens.

docs/operator/oidc-runbooks/okta.md (NEW):
* Okta-specific deltas: Org server vs custom auth server distinction,
  the load-bearing "Define groups claim" step (Okta does NOT emit
  groups by default), group-filter regex on the claim definition,
  access-policy gotcha, optional Okta smoke test pointer to
  Phase 10's integration_okta_smoke_test.go.

docs/operator/oidc-runbooks/auth0.md (NEW):
* Auth0's namespaced-custom-claim quirk documented up front: any
  Action-emitted claim MUST use a URL-shape namespaced key (e.g.
  https://your-namespace/groups), and certctl's hand-rolled
  groupclaim resolver recognizes URL-shape paths as a single literal
  key (no path-walking through `/`). Walks operators through writing
  the Login Action that emits groups from app_metadata. Three
  alternative group-modeling options (app_metadata vs Authorization
  Extension vs Roles+Permissions) with tradeoffs.

docs/operator/oidc-runbooks/azure-ad.md (NEW):
* The big Entra ID quirk documented up front: groups claim emits
  GROUP OBJECT IDs (GUIDs), NOT human-readable names. Certctl group→
  role mappings MUST be configured against the GUIDs. The
  cloud-only-display-names alternative is documented but not
  recommended for hybrid AD environments. Covers the >200 groups
  truncation case (Microsoft's `hasgroups: true` claim) + the v1.0
  vs v2.0 endpoint distinction (certctl supports v2.0 only).

docs/operator/oidc-runbooks/google-workspace.md (NEW):
* The big Google Workspace quirk documented up front: Google does
  NOT emit a groups claim in the ID token. Recommended pattern is
  to broker through Keycloak (or Authentik) as a federated identity
  provider — the user authenticates at Google but certctl talks to
  Keycloak. Walks operators through wiring Google as a federated IdP
  in Keycloak, four group-assignment options (manual vs default-group
  vs claim-derived vs SCIM), and the end-to-end browser flow. The
  "direct integration without groups" anti-pattern is documented at
  the bottom with explicit "NOT RECOMMENDED" framing so operators
  understand why the broker pattern is the right call.

docs/README.md (MODIFIED):
* Adds the OIDC / SSO runbooks index to the operator-facing docs nav
  table, between "Auth threat model" and "Control plane TLS".

Conventions held
================

* Every runbook carries `> Last reviewed: 2026-05-10` per the
  docs convention.
* Every runbook follows the prompt-mandated five-section layout:
  Prerequisites → IdP-side configuration → certctl-side
  configuration → Verification → Troubleshooting → Validation
  checklist (with operator sign-off line).
* Internal-link sweep clean — every relative link resolves to an
  existing file (verified via shell loop checking each `](../...)`
  and `](*.md)` reference). External links to IdP vendor sites are
  the canonical https URLs.
* No leakage of cowork/ workspace paths as Markdown links — the
  azure-ad.md initially had a `[auth-bundles-index.md](../../../../cowork/...)`
  reference; replaced with prose-only mention to match the existing
  convention from rbac.md + migration/api-keys-to-rbac.md.
* The 7 files share a "Validation checklist" footer with operator
  sign-off line; per the prompt's exit criterion, each runbook must
  be validated end-to-end by either the operator or an external
  tester before Bundle 2 ships.

Verification
============

* Last-reviewed dates: 7/7 runbooks dated 2026-05-10.
* Internal-link sweep: 0 broken (every `]( ...)` reference resolves).
* docs/README.md → operator/oidc-runbooks/index.md link resolves.
* No backend / frontend / Go-test impact — pure docs commit. The
  pre-commit `make verify` gate is unchanged; this commit doesn't
  touch any Go file.

Phase 11 deviation note
=======================

The merge-gate criterion's "≥ 2 external testers" requirement is
operator-driven and post-tag — Phase 11 ships the runbooks; the
operator runs each end-to-end against a real production-tier IdP and
fills in the sign-off footers before flipping Bundle 2 to "merged."
Sandbox cannot exercise live Keycloak / Okta / Auth0 / Entra ID /
Google Workspace tenants; the Phase 10 testcontainers Keycloak
integration is the load-bearing automated test on the Keycloak axis,
and the per-IdP runbooks document the manual-validation matrix the
operator runs against the other five IdPs.
2026-05-10 15:49:56 +00:00

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Markdown

# Google Workspace OIDC runbook (broker via Keycloak)
> Last reviewed: 2026-05-10
This runbook wires certctl's OIDC SSO surface against [Google Workspace](https://workspace.google.com/) (formerly G Suite). Google's OIDC implementation has a well-known limitation that makes it unsuitable for direct integration with certctl: **the ID token does not emit a groups claim**, so there is no way for certctl's `ErrGroupsUnmapped` fail-closed contract to resolve a user's role assignment.
The recommended pattern is to **broker Google Workspace through Keycloak (or Authentik)** as a federated identity provider. The end-user still signs in with their Google account, but certctl talks to Keycloak — which DOES emit groups — instead of talking to Google directly.
For the canonical reference + mental model, read [keycloak.md](keycloak.md) first; this runbook builds on top of it.
## The Google Workspace quirk in detail
**What Google emits in an ID token:** `iss`, `aud`, `sub`, `azp`, `exp`, `iat`, `email`, `email_verified`, `name`, `picture`, `given_name`, `family_name`, `locale`, `hd` (hosted domain). That's it.
**What it does NOT emit:** `groups`, `roles`, `permissions`, or any indicator of the user's Google Workspace organizational unit / group membership.
There is a **Cloud Identity Groups API** at `https://cloudidentity.googleapis.com/v1/groups/-/memberships:searchTransitiveGroups` that lets a privileged service account look up a user's groups, but:
1. It requires a service account with domain-wide delegation, which is a major security surface to grant to certctl.
2. It's a separate REST call after the OIDC flow, not a claim — certctl's group-claim resolver is path-shape, not API-shape.
3. The latency budget of an extra API call per login is non-trivial in steady state.
For these reasons, the broker pattern is strongly preferred. If you absolutely cannot deploy a broker, see "Direct integration without groups" at the bottom of this runbook for a degraded mode where every Google-authenticated user gets a single fixed role.
## Architecture: broker pattern
```
end user → Google Workspace login → Keycloak (federated IdP) → certctl
adds groups claim from Keycloak's group store
(NOT from Google)
```
In this topology:
- The end user's authentication credentials live at Google.
- The user's group / role assignments live at Keycloak (manually or via SCIM provisioning from Google).
- certctl talks ONLY to Keycloak. From certctl's perspective this is identical to the [keycloak.md](keycloak.md) runbook.
## Prerequisites
- A running Keycloak instance with a realm dedicated to certctl. Read [keycloak.md](keycloak.md) and complete that runbook FIRST against a local-only test user. Verify end-to-end OIDC works against Keycloak before adding Google as a federated provider.
- A Google Workspace tenant where you have Super Admin access OR can ask your Workspace admin to create OAuth credentials.
- A Google Cloud project (free; same console as Workspace).
## IdP-side configuration
### Step 1: create a Google OAuth client
In the Google Cloud Console (`https://console.cloud.google.com/`):
**APIs & Services → OAuth consent screen → Configure**:
- User Type: **Internal** (restricts to your Workspace domain) OR **External** (any Google account; usually NOT what you want for an internal cert-management tool).
- App name: `certctl SSO via Keycloak`.
- User support email: your team's address.
- Authorized domains: add the domain Keycloak runs on.
- Save.
**APIs & Services → Credentials → Create Credentials → OAuth client ID**:
- Application type: **Web application**.
- Name: `certctl-via-keycloak`.
- Authorized redirect URIs: `https://<keycloak-host>/realms/<realm-name>/broker/google/endpoint` — this is Keycloak's default federated-IdP callback URL. Get the exact URL from Keycloak in step 2 below.
- Click **Create**.
Copy the **Client ID** and **Client secret**.
### Step 2: add Google as a federated identity provider in Keycloak
In the Keycloak admin console (`https://<keycloak-host>/admin/`):
**Realm → Identity providers → Add provider → Google**:
- Alias: `google` (becomes part of the broker URL).
- Display name: `Google Workspace`.
- Client ID: paste from step 1.
- Client secret: paste from step 1.
- Default scopes: `openid profile email`.
- Hosted Domain: your Workspace domain (e.g. `example.com`); restricts to your tenant.
- Sync mode: **Force** (rewrites the user's first/last name/email from Google on every login; the alternative `Import` only writes on first login).
- Trust email: **on** (Google verifies emails; certctl-Keycloak chain inherits the trust).
- Click **Save**.
The **Redirect URI** field at the top of the saved provider's page shows the exact URL you should have entered in Google's console at step 1. Re-verify match.
### Step 3: configure group assignment in Keycloak
This is the load-bearing step — we're explicitly NOT trusting Google for groups, so Keycloak has to provide them.
**Option A: Manual group assignment in Keycloak.**
Federated users from Google appear in **Users** in Keycloak after their first login. You assign them to `certctl-engineers` / `certctl-viewers` / etc. groups in Keycloak's UI manually. Pro: simple. Con: doesn't scale; new hires can't log in until an operator adds them to a group.
**Option B: Default groups via "Default Groups" realm config.**
**Realm settings → User registration → Default Groups → Add**: pick the lowest-privilege group (e.g. `certctl-viewers`). Every new federated user lands here automatically; operators promote individual users to higher groups as needed.
**Option C: Mapper that derives groups from Google claims.**
If your Google Workspace has organizational units that align with your role split, you can add a Keycloak **Identity Provider Mapper** that maps `hd` (hosted domain) or a custom Google directory custom-schema field to a Keycloak group. This is moderately fragile and Workspace-version-dependent; recommend B for most operators.
**Option D: SCIM provisioning from Google to Keycloak.**
Google Workspace can SCIM-push group memberships to Keycloak via the SCIM-for-Google-Cloud-Identity feature. Heavyweight; recommend only if you already have SCIM infrastructure.
This runbook uses **Option B** (default group) for clarity.
### Step 4: verify the broker flow at Keycloak alone
Before bringing certctl into the picture:
1. Log out of Keycloak's admin console.
2. Hit `https://<keycloak-host>/realms/<realm-name>/account` in an incognito window.
3. Click "Sign in" — Keycloak's login page should now show **Sign in with Google Workspace** as a button below the local login form.
4. Click it; authenticate via Google; you should land on Keycloak's account page.
5. Back in the admin console, the user appears under **Users**. Confirm they're in the default group (Option B).
Only proceed to step 5 when Keycloak alone works end to end.
### Step 5: configure certctl against Keycloak (NOT against Google)
Follow the [keycloak.md](keycloak.md) runbook. Use the realm + client + groups configuration you set up there. The `OIDCProvider.issuer_url` is `https://<keycloak-host>/realms/<realm-name>` — Keycloak's URL, not Google's.
When the user clicks "Sign in with Keycloak" on certctl's login page, the browser flow is:
1. certctl → Keycloak authorize endpoint.
2. Keycloak's login page shows **Sign in with Google Workspace** + the local login form. User clicks Google.
3. Keycloak → Google authorize endpoint. User authenticates at Google.
4. Google → Keycloak callback (`/broker/google/endpoint`). Keycloak resolves the user, assigns the default group.
5. Keycloak → certctl callback. certctl sees a normal Keycloak ID token with the `groups` claim populated by Keycloak.
6. certctl mints the session.
End-to-end the user clicks twice (Keycloak's "Sign in with Google" button + Google's consent / login). Subsequent logins skip the consent screen if Google's session is fresh.
## Verification
End-to-end login + audit + Sessions checks are identical to Keycloak. The key Google-Workspace-specific check:
- The `users.oidc_subject` column in certctl's database should contain the Keycloak-side stable subject (a UUID), NOT the Google subject. Decode the certctl-side ID token and confirm `iss` is Keycloak's URL, `sub` is the Keycloak UUID. Don't confuse the certctl ID token with Google's ID token (which lives one hop upstream and certctl never sees directly).
## Direct integration without groups (NOT RECOMMENDED)
If broker deployment is impossible:
1. Configure certctl with `issuer_url = https://accounts.google.com`, `client_id` + `client_secret` from your Google OAuth client (with redirect URI pointed at certctl directly).
2. Add a SINGLE group→role mapping where `group_name` is the empty string. **Wait — certctl rejects empty group names.** This is the structural reason this mode doesn't work: the fail-closed contract requires a real group claim to match.
The actual workaround is to manually add EVERY operator's email to a per-email mapping, OR to add a custom claim emitter at a thin proxy in front of Google. Both are hacks; the broker pattern is strictly better. We document the constraint here so future operators don't burn cycles trying to make it work.
## Troubleshooting
**Federated Google login completes at Keycloak but the user lands on "no roles assigned" at certctl.**
The user authenticated through Google → Keycloak successfully but Keycloak didn't assign them a group (Option A wasn't completed for that user, or Option B's default group isn't mapped on the certctl side). Check:
- Keycloak → Users → <user> → Groups: is the user in any `certctl-*` group?
- certctl → Auth → OIDC Providers → Keycloak → Group → role mappings: is that group mapped?
**Google login fails with "redirect_uri_mismatch".**
The Google OAuth client's authorized redirect URI doesn't match Keycloak's broker callback URL exactly. Re-fetch the URL from Keycloak (Identity Providers → Google → Redirect URI field) and paste it verbatim into Google's console.
**Google auto-closes the consent prompt and returns "access_denied".**
Workspace admin policies may block third-party app access. Either the Google OAuth client wasn't approved by the Workspace admin (Google Workspace Admin Console → Security → API controls → Trusted apps), or the OAuth consent screen is configured for "External" but the user is from a different Workspace. Switch to "Internal" if everyone signing in is in the same Workspace.
**Keycloak log shows "Federated identity returned no email claim".**
You requested OAuth scopes other than `openid profile email`. Re-add `email` to the Default Scopes on the Keycloak Identity Provider config.
**Sign-out from certctl doesn't sign the user out of Google.**
Expected. certctl revokes its own session; Google's session continues independently. If the user needs to fully log out, they sign out at https://accounts.google.com/Logout. The certctl + Keycloak chain is the standard "single sign-on, separate sign-outs" model.
## Validation checklist
Same as [keycloak.md](keycloak.md#validation-checklist), with these additions:
- [ ] Google → Keycloak federation works without certctl in the loop (step 4 above passes).
- [ ] A first-time Google sign-in lands the user in the Keycloak default group (or whatever Option you picked).
- [ ] The certctl audit row's `details.subject` is the Keycloak UUID, NOT Google's `sub` (which would be a Google account ID).
- [ ] Removing a user from Google Workspace causes their NEXT certctl session-validate to fail (after their existing session expires) — verify with a deactivated test user.
Sign-off: _______________ (operator) on _______________ (date).