It’s very convenient to have a program notify you automatically when a new version is released. Typically, the program asks if you want to perform the update, and then completes the process on its own. In fact, security programs like antivirus software are designed to do this every day. As long as I don’t have to waste time fussing with the update, that’s fine by me.

Where developers get into trouble is with the ever more frequent updates that require manually downloading and reinstalling the whole program. I hate that. It wastes time and effort, since my settings are usually wiped out too. I went through this very fiasco today with my instant messaging program, and it took me almost an hour to install the update and fix my preferences afterwards.

If you’re designing a program that requires periodic updates, my advice is to keep the manual upgrades to a minimum. Once a year is fine. But requiring a time-consuming upgrade every few months is definitely going to piss people off.