Since I upgraded my iMac (Late 2012) from Yosemite to Catalina on Feb 3 2020, when I shutdown, my screen first blinks black for a fraction of a second, then remains stuck for 1-2 minutes on my desktop picture, without my desktop items which were cleared upon the blink. It resumes proceeding by going to a restart without shutting down. Upon re-start, I am prompted "Your iMac did not shutdown properly... Do you want to re-open with the previous windows opened?" ( ...Bla bla bla...)
Any how, it might shut down well next time, whatever app is on or off. And it also might get stucked.
The problem is intermittent.
My computer is clean and was working perfectly on Yosemite.
I went through every fix up procedures provided by Apple after discussing the problem with them, competent staff.
Nothing helps or explains what is happening.
In my opinion, Catalina seems to be the problem of that shutdown problem.