Good testing again. I have to ask some basic assumption/questions just to make sure I get the problem:
After a system update that updates Python that new Python version no longer allows port 80. That's the root cause I guess.
Scenario 1: If you have run the system upgrade yourself on the command line you should of course run the install-picochess again (with pico parameter to make it faster).
I guess the problem is scenario 2: User can run system upgrade from the shutdown menu or from some other menu. Now we have the challenge that how to allow Python port 80 in that case without requiring any command to run install-picochess again...
One possible hardwire could be to add a setcap command to the picochess-updater service that always starts and looks for a flag file and if a flag file is found it runs install-picochess... but we could make it always run the setcap even in the situation where no flag was found, ....?
-- Johan