Jan Miksovsky wrote a while back about the dirty business of software updates. He describes the difficulty rich client software developers have with updating their software once it’s in the field (truer words were never spoken…it’s a serious pain), and discusses the relative ease with which our Web-only brethren update their bits. Ultimately, Jan dives into the best experiences you can provide to users while managing their update experience, how Firefox handles it (well, but too many dialogs), and how Microsoft kinda-sorta gets it right. As always, Jan’s interesting, insightful, and far too smart for his own good ;-)

[T]he toast has actually tricked the user into starting the upgrade process. (For the record, this particular upgrade to MSN Messenger Version 7.5 will require a reboot.) The user can try to leave, but only by being forced to agree to be bothered again later. The user can click yet another button to see a web page that (finally) tells them why they should care about this upgrade...It's interesting to wonder which of the features listed above was the one that required a reboot.