Hi Nick,
I have one addition to Roland's comments.
b) Don't call setContentLength, or set it to -1 in a FilePart object. This should work fine with HTTP/1.1 and chunked encoding, but also with HTTP/1.0 and no chunked encoding. Since the server does not know the content length in advance, it has to read until the end of the stream in no-chunks mode. Connection re-use is impossible, but after transferring more than 2 gigs I doubt you'll notice the performance impact of opening a new connection :-) It might be a violation of HTTP to POST data without a valid content length, but since you're controlling the server as well, that shouldn't bother you much.
The HttpClient 2.0 API does not directly support setting content length > 2GB because of the use of an int. This has been fixed in the 3.0 API but it can be done in 2.0 by setting the content-length header manually:
method.setRequestHeader("Content-Length", "Some number bigger than 2GB");
Mike
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