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What tools do you use for the monitoring, backup and rollback?
I use rsync to backup, I can delete and restore the whole drive if i want at any time.
I use watchtower to keep things updated. If you schedule the rsync and watchtower correctly, you can get the backup done before the upgrade and there's basically no lost data with the rollback.
I use uptime Kuma for monitoring, and it shoots me an email with details on what failed.
OpenMediaVault does this as well if you use the built in Docker system. I have it set to back up containers every Sunday at 1 am, at which time it pulls any new images. You can set the number of backups to retain and roll back if there are any issues.