diff --git a/chart/templates/api-server/api-server-deployment.yaml b/chart/templates/api-server/api-server-deployment.yaml
index 03bfe12c3d529..f6591fedb177b 100644
--- a/chart/templates/api-server/api-server-deployment.yaml
+++ b/chart/templates/api-server/api-server-deployment.yaml
@@ -87,6 +87,9 @@ spec:
         checksum/airflow-config: {{ include (print $.Template.BasePath "/configmaps/configmap.yaml") . | sha256sum }}
         checksum/extra-configmaps: {{ include (print $.Template.BasePath "/configmaps/extra-configmaps.yaml") . | sha256sum }}
         checksum/extra-secrets: {{ include (print $.Template.BasePath "/secrets/extra-secrets.yaml") . | sha256sum }}
+        {{- if not .Values.jwtSecretName }}
+        checksum/jwt-secret: {{ include (print $.Template.BasePath "/secrets/jwt-secret.yaml") . | sha256sum }}
+        {{- end }}
         {{- if .Values.airflowPodAnnotations }}
           {{- toYaml .Values.airflowPodAnnotations | nindent 8 }}
         {{- end }}
diff --git a/chart/templates/scheduler/scheduler-deployment.yaml b/chart/templates/scheduler/scheduler-deployment.yaml
index 6b4234af8dea4..d3d68a22f68e8 100644
--- a/chart/templates/scheduler/scheduler-deployment.yaml
+++ b/chart/templates/scheduler/scheduler-deployment.yaml
@@ -102,6 +102,9 @@ spec:
         checksum/airflow-config: {{ include (print $.Template.BasePath "/configmaps/configmap.yaml") . | sha256sum }}
         checksum/extra-configmaps: {{ include (print $.Template.BasePath "/configmaps/extra-configmaps.yaml") . | sha256sum }}
         checksum/extra-secrets: {{ include (print $.Template.BasePath "/secrets/extra-secrets.yaml") . | sha256sum }}
+        {{- if and (semverCompare ">=3.0.0" .Values.airflowVersion) .Values.apiServer.enabled (not .Values.jwtSecretName) }}
+        checksum/jwt-secret: {{ include (print $.Template.BasePath "/secrets/jwt-secret.yaml") . | sha256sum }}
+        {{- end }}
         {{- if .Values.scheduler.safeToEvict }}
         cluster-autoscaler.kubernetes.io/safe-to-evict: "true"
         {{- end }}