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Never upgrade Ubuntu. Just reinstall. It's not that user-friendly.

Believe it or not, I've upgraded Ubuntu successfully several times through the GUI. Before Ubuntu 7.x this tended to fail spectacularly though. It's a very friendly process when it works, which admittedly seems contingent on the maturity of the release in question.

I've done the Ubuntu GUI-based in-place upgrade for the last three releases, if I count back correctly. Aside from the usual point issues in peripheral things that show up when you agree to use a beta (spotty sound in one old game, e.g.), the actual upgrade itself has worked correctly every time.

The concept or way to upgrade it is ok... it's just that it almost always causes a lot more trouble than a clean install.

My experiences so far : 6->7 : System failure, unable to boot 8.04 -> 8.10 : Alright overall, a few bugs to fix (most concerned X) 8.10 -> 9.04 : Better, still a few bugs (info tooltips, graphic card drivers)

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