I'm also having trouble with uploading to pypi, it's not random,
meaning it's happened every time so far. My last upload was about a
week ago and seamless.

Here is my best reconstruction of today:

{{{
python setup.py sdist upload

...snip
adding 'leo-4.11.devel-build-5802\leo.egg-info\PKG-INFO'
adding 'leo-4.11.devel-build-5802\leo.egg-info\SOURCES.txt'
adding 'leo-4.11.devel-build-5802\leo.egg-info\top_level.txt'
removing 'leo-4.11.devel-build-5802' (and everything under it)
running upload
submitting d:/leo/dist\leo-4.11.devel-build-5802.zip to
http://pypi.python.org/pypi
upload failed (500): There's been a problem with your request

python setup.py sdist upload
:: same error

python setup.py register
:: was okay

python setup.py sdist upload
:: same error
}}}

I then went to https://pypi.python.org/pypi?%3Aaction=pkg_edit&name=leo
and noticed that I had my role mysteriously expanded to include Owner
as well as Maintainer.

I used the web interface and removed the Owner role for myself, and
then manually uploaded the sdist package, which succeeded.

Went back to cmd shell and:

{{{
B:\apps\leo\pypi-411>python setup.py bdist_wininst upload

...snip
adding 'SCRIPTS\leoc-script.py'
adding 'SCRIPTS\leoc.exe'
adding 'SCRIPTS\leoc.exe.manifest'
removing 'd:/leo/build' (and everything under it)
running upload
Submitting d:/leo/dist\leo-4.11.devel-build-5802.win32.exe to
http://pypi.python.org/pypi
Server response (200): OK
Submitting d:/leo/dist\leo-4.11.devel-build-5802.win32.exe to
http://pypi.python.org/pypi
Upload failed (400): A file named
"leo-4.11.devel-build-5802.win32.exe" already exists for
leo-4.11.devel-build-5802. To fix problems with that file you should
create a new release.
}}}

Note the double upload.

Going back to the website https://pypi.python.org/pypi/leo there are
now 2 packages listed: "leo 4.10-final", which corresponds to the
sdist package, and "leo 4.11.devel-build-5802" corresponding the win32
.exe installer.

The metadata for 4.10-final has the correct author and maintainer, but
all the other metadata is old and hasn't been updated.

The metadata for 4.11-devel is up to date for homepage through
maintainer but has the wrong Author and is missing the long
description.

The journal entries for the 2 packages mirror each other except for
the last line:
{{{
Journal
Action  Date    User    Address
create  2003-10-09 17:32        edreamleo       66.168.19.217
add Owner edreamleo     2003-10-09 17:32        edreamleo       66.168.19.217
new release     2012-03-29 13:53        edreamleo       68.185.171.138
add Maintainer maphew   2013-05-07 13:08        edreamleo       172.8.201.39
add Owner maphew        2013-05-22 23:21        maphew  199.247.128.35
update _pypi_hidden     2013-05-22 23:22        maphew  199.247.128.35
update _pypi_hidden     2013-05-31 16:52        maphew  199.27.75.22
remove Owner maphew     2013-05-31 16:53        maphew  199.27.75.22
update hosting_mode     2013-05-31 16:56        maphew  199.27.75.20
add source file leo-4.11.devel-build-5802.zip   2013-05-31 16:59
        maphew  199.27.75.21
}}}

{{{
add any file leo-4.11.devel-build-5802.win32.exe        2013-05-31 17:02
        maphew  199.27.75.23
}}}

Also curious is that all the ip addresses for today are wrong and
variable. My external-to-world-ip should be 199.247.128.35 and static.

cheers,

-matt
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