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This is basically the dockerfile these projects provide, so I guess I could do this myself. How do you keep the caddy container up to date? I have tugtainer (something like watchtower) update caddy automatically, but I guess this set up would break that
I can't help you with automation. I update my containers manually, whenever I think to do it. Nothing is accessible outside my network so I'm not worried about staying on top of security updates.
Does tugtainer (always makes me giggle) have to ability to label containers for exclusion like watchtower does?
Yup. It's basically watchtower with a gui
Well, what I was thinking/spitballing is that you could label your Caddy container, do updates on everything else. That leaves Caddy to administer when you can devote 15/20 minutes to rebuilding the Caddy container by itself. Not the most graceful, automated solution, but........