pschoenmakers-ah opened a new issue, #29650:
URL: https://github.com/apache/airflow/issues/29650

   ### Official Helm Chart version
   
   1.8.0 (latest released)
   
   ### Apache Airflow version
   
   2.5.1
   
   ### Kubernetes Version
   
   1.23.16 (rancher-desktop on windows)
   
   ### Helm Chart configuration
   
   After succesful installation of the chart I create a "values" file to add 
the webserver key as per official documentation. No further changes.
   `helm show values apache-airflow/airflow > airflow.yaml`
   
   ### Docker Image customizations
   
   No customisation
   
   ### What happened
   
   After generating the "airflow.yaml" file and adding the webserver secret key 
the upgrade fails
   
   `helm upgrade --install airflow apache-airflow/airflow -n airflow -f 
airflow.yaml --debug`
   Gives output
   
   ```
   history.go:56: [debug] getting history for release airflow
   upgrade.go:142: [debug] preparing upgrade for airflow
   Error: UPGRADE FAILED: execution error at 
(airflow/charts/postgresql/templates/secrets.yaml:20:15): 
   PASSWORDS ERROR: The secret "airflow-postgresql" does not contain the key 
"password"
   
   helm.go:84: [debug] execution error at 
(airflow/charts/postgresql/templates/secrets.yaml:20:15): 
   PASSWORDS ERROR: The secret "airflow-postgresql" does not contain the key 
"password"
   
   UPGRADE FAILED
   main.newUpgradeCmd.func2
        helm.sh/helm/v3/cmd/helm/upgrade.go:201
   github.com/spf13/cobra.(*Command).execute
        github.com/spf13/[email protected]/command.go:872
   github.com/spf13/cobra.(*Command).ExecuteC
        github.com/spf13/[email protected]/command.go:990
   github.com/spf13/cobra.(*Command).Execute
        github.com/spf13/[email protected]/command.go:918
   main.main
        helm.sh/helm/v3/cmd/helm/helm.go:83
   runtime.main
        runtime/proc.go:250
   runtime.goexit
        runtime/asm_amd64.s:1571
   
   ```
   When inspecting the secret the key "password" indeed is not there. Instead 
it has "postgres-password"
   
![image](https://user-images.githubusercontent.com/78535512/220280626-4c04a19a-f94a-4498-88a8-916e47c7e816.png)
   To attempt to let the upgrade continue I added an extra key "password" in 
the secret with the same value.
   The upgrade now indeed proceeds but gets stuck on the migrations step 
   
   `client.go:540: [debug] Watching for changes to Job 
airflow-run-airflow-migrations with timeout of 5m0s
   client.go:568: [debug] Add/Modify event for airflow-run-airflow-migrations: 
ADDED
   client.go:607: [debug] airflow-run-airflow-migrations: Jobs active: 0, jobs 
failed: 0, jobs succeeded: 0
   client.go:568: [debug] Add/Modify event for airflow-run-airflow-migrations: 
MODIFIED
   client.go:607: [debug] airflow-run-airflow-migrations: Jobs active: 1, jobs 
failed: 0, jobs succeeded: 0`
   
   After some time the upgrade fails on a timeout.
   ```
   upgrade.go:434: [debug] warning: Upgrade "airflow" failed: post-upgrade 
hooks failed: timed out waiting for the condition
   Error: UPGRADE FAILED: post-upgrade hooks failed: timed out waiting for the 
condition
   helm.go:84: [debug] post-upgrade hooks failed: timed out waiting for the 
condition
   UPGRADE FAILED
   main.newUpgradeCmd.func2
        helm.sh/helm/v3/cmd/helm/upgrade.go:201
   github.com/spf13/cobra.(*Command).execute
        github.com/spf13/[email protected]/command.go:872
   github.com/spf13/cobra.(*Command).ExecuteC
        github.com/spf13/[email protected]/command.go:990
   github.com/spf13/cobra.(*Command).Execute
        github.com/spf13/[email protected]/command.go:918
   main.main
        helm.sh/helm/v3/cmd/helm/helm.go:83
   runtime.main
        runtime/proc.go:250
   runtime.goexit
        runtime/asm_amd64.s:1571
   ```
   
   ### What you think should happen instead
   
   As with the 1.7.0 version of the chart I expect the webserver key to be 
applied without error messages
   
   ### How to reproduce
   
   - Install rancher-desktop 
   - Make sure it has dockerd container engine and kubernetes 1.23.16 activated
   - Install chart 1.8.0 as per 
https://airflow.apache.org/docs/helm-chart/stable/index
   - create a values file and add a webserverSecretKey as per documentation
   - Attempt an upgrade using the adjusted values file
   
   
   ### Anything else
   
   I tried to install chart 1.7.0 by adding --version 1.7.0 but that also fails 
on the postgres secret, where the keys are now different. When adding the 
missing ones in this attempt an error gets thrown that postgres cannot be 
upgraded at all.
   
   ### Are you willing to submit PR?
   
   - [ ] Yes I am willing to submit a PR!
   
   ### Code of Conduct
   
   - [X] I agree to follow this project's [Code of 
Conduct](https://github.com/apache/airflow/blob/main/CODE_OF_CONDUCT.md)
   


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