martincekada opened a new pull request, #66468:
URL: https://github.com/apache/airflow/pull/66468

   ## Root cause
   
   The api-server deployment template 
(`chart/templates/api-server/api-server-deployment.yaml`) has `checksum/...` 
annotations for several config sources — `airflow-config`, `extra-configmaps`, 
`extra-secrets`, `metadata-secret`, `pgbouncer-config-secret`, and (since 
#60111) `jwt-secret` — but is missing one for the api-server ConfigMap rendered 
from `apiServer.apiServerConfig`.
   
   When users change `apiServer.apiServerConfig`:
   
   - The `airflow-api-server-config` ConfigMap is updated.
   - The api-server deployment's pod template hash is **not** bumped, so no 
rolling restart happens.
   - The api-server pods keep running with the previous `webserver_config.py`. 
The mount uses `subPath`, so kubelet does not auto-refresh the file inside 
running pods either.
   
   The user-visible symptom is that custom auth/security changes silently fail 
to take effect after `helm upgrade` until someone manually runs `kubectl 
rollout restart deploy/<release>-api-server`.
   
   ## Solution
   
   Add a `checksum/api-server-config` annotation to 
`chart/templates/api-server/api-server-deployment.yaml`, guarded by the same 
condition that controls whether 
`chart/templates/configmaps/api-server-configmap.yaml` actually renders:
   
   ```yaml
   {{- if and .Values.apiServer.apiServerConfig (not 
.Values.apiServer.apiServerConfigConfigMapName) }}
   checksum/api-server-config: {{ include (print $.Template.BasePath 
"/configmaps/api-server-configmap.yaml") . | sha256sum }}
   {{- end }}
   ```
   
   This mirrors the pattern used in #60111 for `checksum/jwt-secret`. Same 
shape of bug, same shape of fix, +3/0 in one template.
   
   ## Changes
   
   - Added `checksum/api-server-config` annotation to the api-server deployment 
template.
   - Conditional matches the api-server ConfigMap render condition: only when 
`apiServer.apiServerConfig` is set and `apiServer.apiServerConfigConfigMapName` 
is not (i.e., when the chart manages the ConfigMap).
   
   closes: #66467
   
   ---
   
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