I used to have my docker updates done automatically. However, as the services I used to run just for myself have started to be used by other people (family, friends), I am less tolerant of having things break. So, instead of something like watchtower, I run diun these days. I have it set up to ping me in a discord channel when a docker update is available. Then, I can actually perform the update when I have time and attention to troubleshoot any issues that may come up.