Donald Stufft <don...@stufft.io> added the comment:

> Does PyPI support other digests, e.g. SHA2-256 digest?

There is a simple and a complicated answer to this.

The simple answer is yes, PyPI supports uploads with any combination of MD5, 
SHA256, and blake2_256 (blake2b with a 256 digest, no personalization or key). 
It will also compute all 3 on an upload on it's own and verify that they match 
any provided hashes and to fill in any missing hashes.

The more complicated answer is the upload API is an old API from long before we 
started documenting and standardizing them, so when you start talking about non 
PyPI implementations of that API, what they support is kind of a big who knows.

More to the problem at hand:

We don't rely on this hash for security (We couldn't, it comes in the exact 
same payload as the artifact itself from the exact same source, someone who can 
modify the artifact en route can modify the hash too). So the inclusion of MD5 
is not a concern.

Removing it *might* break non-PyPI servers that attempted to implement this API 
and assumed it was a mandatory field (though I do not have any a priori 
knowledge of this being the case).

Adding additional hashes *might* break non-PyPI servers that assumed what 
distutils used to send was all it would ever send (this is unlikely though, 
most web tools ignore unknown form fields).

I looked into what twine is doing here, and it appears it is sending md5, 
sha256, and blake2_256 hashes all along with every request. However if FIPS 
mode has disabled MD5 it just skips generating and sending MD5 (but still sends 
the other two) and it appears it's done this for 2+ years.

It's probably safe to just mimc what twine is doing here, sending all 3 hashes, 
skip MD5 if it's unavailable.

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