On the one hand, if I run Duplicati first, I can roll back to a previous version if there’s an issue with an update.
On the other hand, if I run Watchtower first, I’m backing up the latest version.
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“On the other hand, if I run Watchtower first, I’m backing up the latest version.”
This makes no sense. I hope you are backing up the persistent data, not the Docker-Images.So before and after Watchtower is identically in the best case scenario.
(In the worst case scenario, after the docker update your persistent data are corrupted because of an bad version update. So the backup should always be before)
Updates can modify persistent data to be non backwards compatible anyways, so it’s even more important to back up beforehand