Hmm… When using WordPress 2.5.2’s media uploads I can upload images from Firefox 3 when running Vista. But I can’t when running FF3 from Ubuntu. Last I checked they’re running the same extensions.
No luck from Opera/Linux either. With either case, I end up with an HTTP error.
Guess I have some research to do. Switching to Linux without Windows Live Writer is hard enough, but if I can’t upload images with the built-in editor it’ll sure get harder!
If I have to guess, I’ll guess Flash based on this support forum post… that’s where I’ll start, at any rate.
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July 5th, 2008 
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My guess would be a Flash issue. 2.6 allows you to also use the previous, non-flash uploader.
Definitely the flash issue. 2.6 and the other uploader are working just fine.