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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.

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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.

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