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It appears that with Python 3.2 (Windows 64-bit), the distutils upload -r command no longer accepts the repository section name, but instead only attempts to parse it as a URL. This is a regression from Python 2.7.
PS C:\Users\jaraco\projects\hgtools> python -m pdb setup.py sdist upload -r pypi
> c:\users\jaraco\projects\hgtools\setup.py(7)<module>()
-> """
(Pdb) c
running sdist
running egg_info
# lines elided
running upload
Submitting dist\hgtools-1.0b1.zip to pypi
Traceback (most recent call last):
 File "c:\python\lib\pdb.py", line 1556, in main
 pdb._runscript(mainpyfile)
 File "c:\python\lib\pdb.py", line 1437, in _runscript
 self.run(statement)
 File "c:\python\lib\bdb.py", line 392, in run
 exec(cmd, globals, locals)
 File "<string>", line 1, in <module>
 File "c:\users\jaraco\projects\hgtools\setup.py", line 7, in <module>
 """
 File "c:\python\lib\distutils\core.py", line 149, in setup
 dist.run_commands()
 File "c:\python\lib\distutils\dist.py", line 919, in run_commands
 self.run_command(cmd)
 File "c:\python\lib\distutils\dist.py", line 938, in run_command
 cmd_obj.run()
 File "c:\python\lib\distutils\command\upload.py", line 66, in run
 self.upload_file(command, pyversion, filename)
 File "c:\python\lib\distutils\command\upload.py", line 176, in upload_file
 raise AssertionError("unsupported schema "+schema)
AssertionError: unsupported schema
Uncaught exception. Entering post mortem debugging
Running 'cont' or 'step' will restart the program
> c:\python\lib\distutils\command\upload.py(176)upload_file()
-> raise AssertionError("unsupported schema "+schema)
(Pdb) self.repository
'pypi'
(Pdb) schema
''
(Pdb) q

I started working on a test for this in packaging and it’s worse than I expected: it does not support multiple repositories at all. The config parser has bogus tests and the upload command has no test for this. I will work on fixing this in packaging and backport.

This is a strange bug. I added a test using -r server2, using the already-existing PYPIRC_LONG_PASSWORD string as .pypirc contents. The test passes. To make sure changing one test would not affect another one, I created a new .pypirc file, PYPIRC_CUSTOM_SERVER, and then I got to see your bug! I tried various combinations of keys (realm or not, user or not), changed the markup (: or = as delimiter, spaces or not) but could not easily find the root of the bug.
Can you publish a .pypirc file that works with 2.7 and not with 3.2? That would be a good starting point.

I now seem to be unable to reproduce the issue. I do keep my .pypirc in a revision control system, so I have reasonable confidence that my .pypirc contained the content that I'm attaching now (passwords scrubbed of course).
One possible factor is that my .pypirc is symlinked from ~/.pypirc to config/python/.pypirc and it's conceivable that Python 3.2.0 has some issues with symlink resolution that caused it to not process the .pypirc properly.
I'm going to install Python 3.2.0 and try to reproduce the issue there.

Sure enough. I just confirmed that with Python 3.2.0, if .pypirc is symlinked, distutils behaves as if the .pypirc isn't present at all, but if that same .pypirc is copied, it behaves as expected. If one deletes the .pypirc altogether, it produces the same error.
Furthermore, this issue was fixed before the release of 3.2.2 (probably in 3.2.1).
My guess is that with the PYPIRC_CUSTOM_SERVER, it was somehow not being installed or resolved correctly, so the content was irrelevant.
I suggest we mark this bug as resolved (as the primary cause was due to the file not being read at all), but also apply your patch (which has some other good fixes) without the CUSTOM_SERVER, or with a version of the CUSTOM_SERVER that works.

[copy/paste failure in my previous message, please disregard]
> One possible factor is that my .pypirc is symlinked from ~/.pypirc to config/python/.pypirc and
> it's conceivable that Python 3.2.0 has some issues with symlink resolution that caused it to not
> process the .pypirc properly.
Are these Windows symlinks? Are they supposed to be dereferenced transparently by the OS (i.e. during open) like unix symlinks?
> Sure enough. I just confirmed that with Python 3.2.0, if .pypirc is symlinked, distutils behaves
> as if the .pypirc isn't present at all, but if that same .pypirc is copied, it behaves as
> expected. If one deletes the .pypirc altogether, it produces the same error.
OK. For distutils2, I think we’ll want better logging/error reporting. The user should see "no /what/ever/.pypirc found", not "section not found".
> I suggest we mark this bug as resolved (as the primary cause was due to the file not being read at
> all), but also apply your patch (which has some other good fixes) without the CUSTOM_SERVER, or
> with a version of the CUSTOM_SERVER that works.
Agreed. I’ll resume work on that patch to understand why it fails.

Windows symlinks, much like Unix symlinks, should dereference naturally when open is called, although there is a bug in later versions of the c runtime calling stat on a symlink. See issue6727 for details.

So, if upload command never accepted repository by section name I am +1 for closing this issue (and opening a new one if symlink workaround is required).

If you read the first message again, or the docs, you can see that -r repo-name was indeed supported.

Indeed, the issue as reported is invalid.