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I guess trying to debug this when it's happening could be worthwhile - your explanation sounds credible - if I can execute a few things from the command line to try and chase this down, I'd be happy to give it a go.
For debugging HTTP, try Charles - it's available for Windows, Linux and OS X and allows you to inspect the HTTP traffic between your browser and the net, allowing you to check headers and so forth. The trial version puts up the occasional nag screen and only runs for thirty minutes, but that's probably all you need anyway - if you can see that a file which contains some particular content doesn't have a Content-Type header, but when accessed from Windows it does, then it may be an Ubuntu problem.
The tricky bit is that, if some of 3's network is misconfigured, you don't know if you're connecting to a working bit or not, so you'd have to disconnect and reconnect several times to see what's going on.



