## Customer-reported bug
A customer hit this when using the AI chat:
```json
{
"message": "API key 760d4822-da40-4b3f-9031-40563d7ed6c9 has no role assigned",
"extensions": {
"code": "INTERNAL_SERVER_ERROR",
"userFriendlyMessage": "This API key has no role assigned."
}
}
```
Their integration authenticates via API key. Somewhere along the way,
the role bound to that API key was deleted, leaving the API key
authenticated but role-less. Any request that hits a permission check
(`getRoleIdForApiKeyId`) blows up.
## Root cause
In `RoleService.deleteManyRoles`, the pre-deletion cleanup
(`assignDefaultRoleToMembersWithRoleToDelete`) only rebinds **user
workspaces** to the workspace default role. API keys and agents pointing
at the role are ignored. Because `RoleTargetEntity.role` declares
`onDelete: 'CASCADE'`, the FK then drops the role_target rows for those
API keys / agents — but the API keys themselves stay in `api_key`, now
orphaned in `apiKeyRoleMap`.
A previous read-side workaround
([2767ddac44](https://github.com/twentyhq/twenty/commit/2767ddac44) —
make the `role` ResolveField nullable) handled the API-key-details page,
but did not address the write paths (`getRoleIdForApiKeyId`).
## Fix
- Rename `assignDefaultRoleToMembersWithRoleToDelete` →
`rebindTargetsOfRoleToDeleteToDefaultRole` and extend it to rebind API
keys (via `ApiKeyRoleService.assignRoleToApiKey`) and agents (via
`AiAgentRoleService.assignRoleToAgent`) in the same step, before the
role is deleted.
- If the workspace default role doesn't satisfy `canBeAssignedToApiKeys`
/ `canBeAssignedToAgents`, the inner `assignRoleTo*` validation throws.
We catch that and rethrow as a `PermissionsException` with a
role-deletion-context message and two new codes —
`ROLE_CANNOT_BE_ASSIGNED_TO_API_KEYS` /
`ROLE_CANNOT_BE_ASSIGNED_TO_AGENTS` — so the admin sees a clear
"reassign these first" prompt rather than a confusing inner error.
## Scope / non-goals
- **Already-orphaned API keys are not auto-healed.** The customer still
needs to reassign a role to their existing orphan API key via the UI
(Settings > API Keys > [the key] > role). A separate cleanup command for
existing orphans is a follow-up.
- I did not investigate *why* the customer's session was authenticated
via API key in the AI chat — that may be their integration setup. Worth
confirming with them separately.
## Test plan
- [ ] Workspace with default role `Admin` (which has
`canBeAssignedToApiKeys: true`): create an API key with a custom role,
delete the custom role → API key is rebound to Admin, requests keep
working.
- [ ] Workspace with default role `Member` (default, has
`canBeAssignedToApiKeys: false`): create an API key with a custom role,
delete the custom role → role deletion fails with the new
`ROLE_CANNOT_BE_ASSIGNED_TO_API_KEYS` error explaining the admin must
reassign first. API key + custom role are both unchanged.
- [ ] Same two scenarios for agents (`canBeAssignedToAgents`).
- [ ] Existing user-workspace rebind behavior is unchanged.
- [ ] Role deletion with no dependent API keys / agents still works.
