Hello @FrancescoDB1, thank you for providing all the details.
I was able to investigate more about this matter and looks like if you received an "optimizing add ons" pop up to update your add ons, it means Outlook is cleaning some things for the add-ons. One of the things that usually gets cleaned is the cache, which deletes any information that the extension has stored.
This is why it gets disconnected and sometimes even uninstalled. Do you get an option to stop the 'Optimizing add-ons' action? Currently, this is done automatically by Outlook and we can't control it, the only way would be to prevent outlook from doing this action.