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Here is a program that demonstrates the problem:
 import httplib
 import tempfile
 f = tempfile.TemporaryFile()
 f.write("Hello, Temporary File!")
 f.seek(0)
 c = httplib.HTTPConnection('bugs.python.org')
 c.request('POST', '/', f, {'Content-type' : 'application/octet-stream'})
 r = c.getresponse()
 print r.status, r.reason
The expected output is "200 OK", and that's what happens on Mac and almost certainly on Linux. On Windows, this is the result:
 Traceback (most recent call last):
 File "bad.py", line 9, in <module>
 c.request('POST', '/', f, {'Content-type' : 'application/octet
 File "C:\Python27\lib\httplib.py", line 958, in request
 self._send_request(method, url, body, headers)
 File "C:\Python27\lib\httplib.py", line 989, in _send_request
 self._set_content_length(body)
 File "C:\Python27\lib\httplib.py", line 964, in _set_content_len
 thelen = str(len(body))
 File "C:\Python27\lib\tempfile.py", line 383, in __getattr__
 a = getattr(file, name)
 AttributeError: 'file' object has no attribute '__len__'
Changing the lines:
 f = tempfile.TemporaryFile()
 f.write("Hello, Temporary File!")
 f.seek(0)
to:
 f = open("temp.file", "w+")
 f.write("Hello, Less Temporary File!")
 f.seek(0)
makes it work on Windows.