I released pyOpenSSL 0.13 a few days ago. Apart from making sure it actually worked on various platforms, updating the version number, regenerating the documentation, and sending out the release announcement, I also had to upload release files to the Python Package Index.
Uploading release files to PyPI is the part of the release process I hate the most. pyOpenSSL 0.13 had 15 files to upload to PyPI. There is no usable automated interface for uploading files to PyPI. Before I can even begin to upload them, I have to download them from the build farm where they're generated. Then, uploading just one file to PyPI requires at least 8 mouse clicks. The clicks vary depending on which file is being uploaded. I have to select a file, select its type, specify which Python version it's for, and then submit a form.
15 files, 8 clicks per file. Well, you do the math. It's not a pleasant experience. PyPI would be a much better resource if it didn't force me to specify a ton of redundant, mostly useless information every time I do a release. It would be a much better resource if it had a programmatic interface so I don't have to spend 20 minutes clicking buttons in web browser. It would be a much better resource if it didn't try to hard to discourage me from releasing software.