We ran some updates recently and a Python 3 version completely screwed up our Chef builds.
When we were trying to upgrade from 7 to 8, all of the instances we tried either broke, failed to upgrade entirely, or would continue looking for 7 repos instead of 8.
I’ve not experienced that with Ubuntu or Debian.
Granted, I’ve inherited this environment, so it could be something in the configuration management/configuration drift. I’ve never had a problem with RHEL/CentOS until I worked here.