I created an issue on setuptools tracker about Windows newlines ( https://github.com/pypa/setuptools/issues/1126), and another on Warehouse about the "Invalid file extension" message and PEP 517 ( https://github.com/pypa/warehouse/issues/2281). I'm not creating one for ignoring duplicated files in `upload` because twine already has this feature (--skip-existing), and other people may be relying on this behavior.
Also, I agree with Nathaniel Smith that numbered versioning of the API (/v0/, /v1/, /v/2) would be preferable to /legacy/.
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