They try pretty hard to do that. The number of things that can go wrong is pretty large. Mostly, if you don’t keep your os up to date (and probably docker) it’s your fault.
They try to check for docker version, and the scripts I use upgrade docker if it’s known to be bad (it should should probably just always upgrade docker).
I think they might do better to always force a command line upgrade if the base image changes at all. I mostly never use it since my dashboard does a command line update with a click.