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Root Cause
The JWT secret checksum annotation was missing from both deployment templates. Other secrets (metadata-secret, pgbouncer-config-secret, etc.) had checksum annotations that trigger pod restarts when secrets change, but the JWT secret did not.
When Helm values change:
The API server redeploys (due to other checksum changes) and picks up the new JWT secret
The scheduler doesn't redeploy (no JWT secret checksum) and continues using the old secret
Tokens generated by the scheduler fail validation at the API server
Solution
Added checksum/jwt-secret annotations to both:
chart/templates/api-server/api-server-deployment.yaml
chart/templates/scheduler/scheduler-deployment.yaml
This ensures both components redeploy together when the JWT secret changes, keeping them synchronized.
Changes
Added JWT secret checksum annotation to API server deployment template
Added JWT secret checksum annotation to scheduler deployment template
Conditional logic matches the JWT secret template (only for Airflow 3.0+ when API server is enabled and chart manages the secret)

closes: #60040

@jscheffl jscheffl merged commit d614e76 into apache:main Jan 5, 2026
93 checks passed
@jscheffl jscheffl added this to the Airflow Helm Chart 1.19.0 milestone Jan 5, 2026
chirodip98 pushed a commit to chirodip98/airflow-contrib that referenced this pull request Jan 8, 2026
apache#60111)

* Add checksum for JWT secret in API server and scheduler deployments if conditions are met

* Update API server deployment to conditionally include JWT secret checksum based on jwtSecretName value
chirodip98 pushed a commit to chirodip98/airflow-contrib that referenced this pull request Jan 9, 2026
apache#60111)

* Add checksum for JWT secret in API server and scheduler deployments if conditions are met

* Update API server deployment to conditionally include JWT secret checksum based on jwtSecretName value
stegololz pushed a commit to stegololz/airflow that referenced this pull request Jan 9, 2026
apache#60111)

* Add checksum for JWT secret in API server and scheduler deployments if conditions are met

* Update API server deployment to conditionally include JWT secret checksum based on jwtSecretName value
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Redeployment of API server without the scheduler causes dag failure

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