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It’s just a hobby so i know I have room for improvement, but the bigger my environment gets the more difficult it is to keep everything completely up to date, like you said. Given that, my main priorities are:
Now that being said, I’ve started to use ansible playbooks for deploying OS updates. I have a playbook that uses default options when doing an apt upgrade and it also works for the docker engine user prompt.
About 75% of my services are native installs in LXCs and I try to always install by including the app repo so that apt can update it and the other 25% are in docker. I used to use watchtower but that’s no longer maintained, so I do container updates manually as needed.
It’s not perfect, but it’s just for fun so 🤷
Hm, I didn't think of ansible, that's something I should think about to use.