It’s a completely fair standpoint. You have to look out for your business first. I’m just the sysadmin trying to weigh some counterpoints because I deal with threat aversion and infrastructure hardening on a day-to-day basis.
Once one has a solution that’s at least good enough people will usually stick with that, which is also fair. I know that the decisionmakers who pay my salary can’t have me follow every tech lead where my hourly wage goes to something that’s not a direct moneymaker.





You’re making a valid point. fwiw I wasn’t trying to advocate for my approach as a best practice I was just saying this is my reality thus far. (I think I’ve been on Vaultwarden for about 2 years now.)
Watchtower itself basically just does “docker pull + down + up” for you, so whether that recreation of the container and any necessary migration work out is up to the software inside. One essential part of my infrastructure that I can think of where breaking changes did necessitate manual intervention was wg-easy my Wireguard container. But that just meant that I was stuck on an outdated version until I transitioned my compose file to get the new stuff. I can’t remember anything ever breaking through an unattended Watchtower update, which maybe I shouldn’t be saying out loud but oh well.