My main thought regarding this is that bdist_dmg != all dmg files (similarly 
for msi and wininst). These are specific files created by distutils without a 
standard or without the needed work to make them truly what users should be 
using. I also think they are a different class of upload, the general use case 
for PyPI's current file uploads are for automated installs (as evidenced by the 
simple API and mirroring).

If we want to enable dmg, msi, etc uploads that are not the bdist_* variety for 
automated tooling, then we could do something like "related files" people can 
upload which don't get mirrored for pip and which don't show up in the repo 
API. Since they will be classified differently we could also do better work 
around the ux of discovering them and separate them from the 50 wheels that 
some projects end up uploading and make them more obviously visible. I don't 
know if pypi as a distribution for _end user_ (vs developer/power user) 
software makes sense or not, but if it does we should support it better than 
accidentally via distutils. 

Sent from my iPhone

> On Aug 15, 2016, at 4:17 PM, Glyph Lefkowitz <gl...@twistedmatrix.com> wrote:
> 
> Anyway, like I said: not an expert here, just wanted to make sure the "python 
> for desktop software (even if it's not used much right now)" angle is 
> considered as well.

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