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Attempting to upload a release, I get a "warning" error.
setuptools main $ .tox/release/bin/python -m twine upload dist/*
Uploading distributions to https://upload.pypi.org/legacy/
Uploading setuptools-62.1.0-py3-none-any.whl
100% ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 1.2/1.2 MB • 00:00 • 6.8 MB/s
WARNING Error during upload. Retry with the --verbose option for more details.
Is it an error or a warning? Why make me retry to get some useful information? Retry with verbose does reveal the cause:
setuptools main $ .tox/release/bin/python -m twine upload dist/* --verbose
Uploading distributions to https://upload.pypi.org/legacy/
INFO dist/setuptools-62.1.0-py3-none-any.whl (1.1 MB)
INFO dist/setuptools-62.1.0.tar.gz (2.4 MB)
INFO username set by command options
INFO Querying keyring for password
INFO password set from keyring
INFO username: __token__
INFO password: <hidden>
Uploading setuptools-62.1.0-py3-none-any.whl
100% ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 1.2/1.2 MB • 00:00 • 5.2 MB/s
INFO Response from https://upload.pypi.org/legacy/:
400 File already exists. See https://pypi.org/help/#file-name-reuse for more information.
INFO <html>
<head>
<title>400 File already exists. See https://pypi.org/help/#file-name-reuse for more information.</title>
</head>
<body>
<h1>400 File already exists. See https://pypi.org/help/#file-name-reuse for more information.</h1>
The server could not comply with the request since it is either malformed or otherwise incorrect.<br/><br/>
File already exists. See https://pypi.org/help/#file-name-reuse for more information.
</body>
</html>
It seems to me twine should provide more useful details on a failed upload during the initial attempt. If the issue was transient, I wouldn't be able to recreate it in a second attempt. Especially for known failure cases, Twine should detect them and report useful information during the initial attempt.