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Automatically upgrading docker images sounds like a recipe for disaster because:
That's why I refuse to automate updates. I sometimes go weeks or months between using a given service, so I'd rather use vulnerable containers than have to go fix it when I need it.
I run OS updates every month or two, and honestly I'd be okay automating those. I run docker pulls every few months, and there's no way I'd automate that.
I've encountered that before with Watchtower updating parts of a serrvice and breaking the whole stack. But automating a stack update, as opposed to a service update, should mitigate all of that. I'll include a system prune in the script.
Most of my stacks are stable so aside from breaking changes I should be fine. If I hit a breaking change, I keep backups, I'll rebuild and update manually. I think that'll be a net time save over all.
I keep two docker lxcs, one for arrs and one for everything else. I might make a third lxc for things that currently require manual updates. Immich is my only one currently.
Glad it works for you.
Automatic updates of software with potential breaking changes scares me. I'm not familiar with watchtower, since I don't use it or anything like it, but I have several services that I don't use very often, but would suck if they silently stopped working properly.
When I think of a service, I think of something like Nextcloud, Immich, etc, even if they consist of multiple containers. For example, I have a separate containers for libre office online and Nextcloud, but I upgrade them together. I don't want automated upgrades of either because I never know if future builds will be compatible. So I go update things when I remember, but I make sure everything works after.
That said, it seems watchtower can be used to merely notify, so maybe I'll use it for that. I certainly want to be around for any automatic updates though.
It's Watchtower that I had problems with because of what you described. Watchtower will drop your microservice, say a database, to update it and then not reset the things that are dependent on it. It can be great just not in the ham fisted way I used it. So instead I'm going to update the stack together, everything drops, updates, and comes back up in the correct order
Uptime Kuma can alert you when a service goes down. I am constantly in my Homarr homepage that tells me if it can't ping a service, then I go investigating.
I get that it's scary, and after my Watchtower trauma I was hesitant to go automatic too. But, I'm managing 5 machines now, and scaling by getting more so I have to think about scale.
I don't use Watchtower myself for the same reasons described, but I was under the understanding if you had a container as a dependency on another container that if you took the dependency down it also took the container down. Is this not actually true?