After every upgrade to a higher version I get the same stupid pop-ups again for the same software, why?
If you wish, you have the option to import the configurations in CIS>Miscellaneous>Manage my Configurations, before updating to the next version.
These are, I think, based on users preferences. Some likes to use it from scratch to explore full possibilities of new upgrade and some likes to retain the old configurations.
CIS, AFAIK, has taken into consideration the wish of both.