certctl/docs/operator/oidc-runbooks/azure-ad.md

Microsoft Entra ID (Azure AD) OIDC runbook

Last reviewed: 2026-05-10

This runbook wires certctl's OIDC SSO surface against Microsoft Entra ID, formerly Azure AD. Entra ID is Microsoft's commercial cloud IdP; it's the default IdP for any organization on Microsoft 365 / Azure.

For the canonical reference + mental model, read keycloak.md first; this runbook only documents the Entra-ID-specific deltas.

The big Entra ID quirk: groups claim emits OBJECT IDs, not names

Entra ID's groups claim emits a JSON array of group object IDs (GUIDs), not human-readable names. A user in Engineering Group and Cert Operators will see something like:

{
  "groups": [
    "8b9b1faa-4e83-471e-8b00-7d99c3e2a5f1",
    "f00cf1e2-2db1-4cdf-a1ba-1234567890ab"
  ]
}

You must configure your certctl group→role mappings against these GUIDs, not against Engineering Group or Cert Operators. There are workarounds (cloud-only group display names + the optional claims path; see the alternative below) but the GUID-based approach is the only one that works reliably across all Entra ID configurations.

This is by design at Microsoft — group names are mutable and not globally unique within a tenant; object IDs are immutable and globally unique. Operators on Microsoft 365 / Azure deployments are accustomed to managing access by GUID.

Prerequisites

On the Entra ID side:

• A Microsoft 365 tenant or standalone Azure AD tenant. Free Azure AD tier is sufficient; paid tiers (P1/P2) unlock conditional access + SCIM provisioning + risk-based auth, none of which are required for the basic OIDC integration.
• Application Administrator or Global Administrator role.
• Network reachability from certctl-server to https://login.microsoftonline.com/<tenant-id>/v2.0/.well-known/openid-configuration.

On the certctl side: same as Keycloak.

IdP-side configuration

1. Register the application

In the Entra ID admin center:

Applications → App registrations → New registration:

• Name: certctl.
• Supported account types: Accounts in this organizational directory only (single-tenant; matches the typical operator use case).
• Redirect URI: Web + https://<your-certctl-host>:8443/auth/oidc/callback.
• Click Register.

On the saved app's Overview page, copy:

• Application (client) ID → certctl's client_id.
• Directory (tenant) ID → goes into the issuer URL.

2. Create a client secret

App → Certificates & secrets → Client secrets → New client secret:

• Description: certctl-server.
• Expires: 6 months / 12 months / 24 months — your choice. Set a calendar reminder; Entra ID does NOT auto-rotate secrets.
• Click Add.

Copy the Value column immediately — it's shown ONCE on creation. The certctl provider's client_secret field gets this value.

(Production hardening: prefer Certificates over secrets for client authentication; certctl currently supports client_secret_post only, but a follow-on bundle can add private_key_jwt for cert-based client auth. Track this if you have a hard requirement against shared secrets.)

3. Add the groups claim to the token

App → Token configuration → Add groups claim:

• Pick Security groups (covers most operators) OR Groups assigned to the application (more granular but requires Premium).
• Token type: ID token + Access token (both, so userinfo fallback works).
• Customize emit format for ID/access: leave as Group ID (default; this is the GUID-based path the runbook is structured around).
• Click Save.

If you instead want display names in the claim (only works for cloud-only groups; on-prem-synced groups continue to emit GUIDs regardless):

• Customize emit format → Cloud-only group display names.
• BUT — note this works only for groups created in Entra ID itself, not groups synced from on-prem AD. Hybrid environments will have inconsistent claims.

4. Add the optional email and profile claims

By default Entra ID's ID token does NOT include email — Microsoft considers email part of the "OIDC profile" but only emits it under specific conditions. To force emission:

App → Token configuration → Add optional claim → ID token → email.

You may also want family_name, given_name, preferred_username for richer User records on the certctl side.

5. Grant the API permissions

App → API permissions:

• Microsoft Graph → Delegated permissions → ensure these are granted (most are default):
  • openid
  • profile
  • email
  • offline_access (optional; for refresh tokens — certctl doesn't use them currently).
• Click Grant admin consent if your tenant requires it.

6. (Optional) Restrict who can sign in

By default any user in your tenant can attempt to sign in to the app. To restrict to specific users / groups:

Enterprise applications → certctl → Properties → Assignment required: Yes. Then Users and groups → Add user/group and pick the cert-engineers / cert-viewers Entra ID groups.

certctl-side configuration

curl -X POST https://<your-certctl-host>:8443/api/v1/auth/oidc/providers \
  -H "Authorization: Bearer ${CERTCTL_API_KEY}" \
  -H "Content-Type: application/json" \
  -d '{
    "name": "Entra ID",
    "issuer_url": "https://login.microsoftonline.com/<tenant-id>/v2.0",
    "client_id": "<application-id>",
    "client_secret": "<client-secret-value>",
    "redirect_uri": "https://certctl.example.com:8443/auth/oidc/callback",
    "groups_claim_path": "groups",
    "groups_claim_format": "string-array",
    "fetch_userinfo": false,
    "scopes": ["openid", "profile", "email"],
    "iat_window_seconds": 300,
    "jwks_cache_ttl_seconds": 3600
  }'

Notes:

• issuer_url MUST include /v2.0 at the end for the v2.0 endpoint. The v1.0 endpoint emits tokens with a different iss shape and is NOT supported by certctl. The discovery doc at https://login.microsoftonline.com/<tenant-id>/v2.0/.well-known/openid-configuration confirms the right path.
• <tenant-id> is the Directory (tenant) ID GUID from step 1.

Add the group→role mappings (GUID-keyed)

Get the GUIDs of your engineering / viewer groups:

Entra ID → Groups → All groups → → Overview → Object ID.

Then in certctl:

# Engineering group → r-operator
curl -X POST https://<your-certctl-host>:8443/api/v1/auth/oidc/group-mappings \
  -H "Authorization: Bearer ${CERTCTL_API_KEY}" \
  -H "Content-Type: application/json" \
  -d '{
    "provider_id": "<provider-id>",
    "group_name": "8b9b1faa-4e83-471e-8b00-7d99c3e2a5f1",
    "role_id": "r-operator"
  }'

Repeat for every group you want to map. Document the GUID-to-name mapping in your operator runbook — without it, the next operator looking at certctl's mappings page sees a wall of GUIDs with no way to know which is which. Consider naming the mapping descriptively if your group-mapping schema supports it (Bundle 2 doesn't yet — group-mapping descriptions are a parking-lot item for a follow-on bundle).

Verification

End-to-end login + audit + Sessions checks are identical to Keycloak.

Entra-ID-specific: the audit row's details.subject will be Microsoft's oid claim (a GUID, the user's object ID), stable across UPN / email changes. The certctl users table's oidc_subject column holds this GUID.

JWKS-rotation: Microsoft auto-rotates signing keys on a documented schedule (every ~6 weeks). The discovery doc + JWKS endpoint always serve the union of active + recently-active keys, so in-flight logins continue to validate. No manual operator action needed in steady state. If you suspect a stuck cache after a Microsoft-side rotation, click "Refresh discovery cache" in the certctl GUI to evict.

Troubleshooting

Login completes; ID token contains a hasgroups: true claim instead of groups.

Entra ID emits this when a user is in too many groups (>200 by default for ID tokens, >150 for access tokens) — Microsoft truncates the claim and tells the consumer to use Microsoft Graph to look up the full list. certctl does NOT currently support the Graph fallback path (it's a follow-on bundle item).

Workarounds:

• Reduce the user's group membership to <200 (rarely practical in large tenants).
• Restrict the groups claim to "Groups assigned to the application" (Token configuration step 3 above) instead of "Security groups". The "assigned" set is bounded by the app's user assignments and stays under the limit.
• Use Entra ID's optional wids (well-known IDs) claim if you only care about admin/non-admin distinction; certctl can be configured against wids by setting groups_claim_path accordingly.

groups claim missing entirely.

Step 3 wasn't completed — Entra ID does NOT emit groups by default. Add the claim via Token configuration before users will see it.

ErrIssuerMismatch even though the tid in the token matches.

The v2.0 endpoint emits iss = https://login.microsoftonline.com/<tenant-id>/v2.0 (no trailing slash). The v1.0 endpoint emits iss = https://sts.windows.net/<tenant-id>/. Confirm certctl's issuer_url matches v2.0 exactly — no trailing slash, includes /v2.0.

On-prem-synced groups emit GUIDs even when "Cloud-only display names" is selected.

Expected behavior — Microsoft only emits display names for groups created in Entra ID itself (cloud-only). On-prem-synced groups always emit object IDs. The hybrid case is unfixable from the IdP side; either map against GUIDs (recommended) or migrate the relevant groups to cloud-only.

The email claim is empty even though the user has a primary email.

Entra ID's email claim only populates when:

1. The user has a "Primary email" set on their Entra ID profile (often blank for B2B guest users).
2. The optional claim was added in step 4.

For B2B guests, the preferred_username claim usually carries the email-shape login. You can configure certctl to use preferred_username as the user's display name fallback, but the User.Email column will remain blank — that's expected for guests.

Conditional Access policies blocking the login.

If your tenant has Conditional Access requiring MFA for new applications, certctl will see the user redirected through the MFA challenge. This works transparently — the certctl service doesn't care that MFA was performed; it only validates the resulting ID token. If MFA is failing for the user, debug at the Entra ID side (Sign-in logs).

Validation checklist

Same as keycloak.md, with these additions:

• The ID token's groups claim is a string-array of GUIDs (decode at jwt.io).
• Each certctl group-mapping uses the GUID, not a human-readable name.
• A user with >200 groups successfully logs in (or the operator has documented the limitation + workaround in their internal runbook).
• The Entra ID Sign-in logs view shows the certctl login event with status "Success".

Sign-off: _______________ (operator) on _______________ (date).