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Fix test_https_over_http_error on Windows with OpenSSL 3.1+ #828

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Fix test_https_over_http_error on Windows with OpenSSL 3.1+ #828

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32 changes: 23 additions & 9 deletions cheroot/test/test_ssl.py
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Original file line number Diff line number Diff line change
Expand Up @@ -527,7 +527,9 @@ def test_tls_client_auth( # noqa: C901, WPS213 # FIXME
"'Remote end closed connection without response'))",
)

assert any(e in err_text for e in expected_substrings)
assert any(e in err_text for e in expected_substrings), (
f'Unexpected error text: {err_text!r}'
)


@pytest.mark.parametrize( # noqa: C901 # FIXME
Expand Down Expand Up @@ -697,14 +699,26 @@ def test_https_over_http_error(http_server, ip_addr):
http.client.HTTPSConnection(
f'{interface}:{port}',
).request('GET', '/')
expected_substring = (
'record layer failure'
if IS_ABOVE_OPENSSL31
else 'wrong version number'
if IS_ABOVE_OPENSSL10
else 'unknown protocol'
)
assert expected_substring in ssl_err.value.args[-1]
underlying_error_string = str(ssl_err.value)
if IS_ABOVE_OPENSSL31 and IS_WINDOWS:

@webknjaz webknjaz Jul 7, 2026

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@julianz- looks like it's not just Windows: https://github.com/cherrypy/cheroot/actions/runs/28048216203/job/83032035095?pr=828#step:15:131

# On Windows, the TCP reset (RST) is surfaced before OpenSSL processes
# the server's response, yielding 'wrong version number' rather than
# the usual 'record layer failure'. See CPython's own test_ssl.py:
# https://github.com/python/cpython/blob/\
# 1b9fe5c7226eccc8b269a7443148033080399f43\
# /Lib/test/test_ssl.py#L5705
assert 'wrong version number' in underlying_error_string
elif IS_ABOVE_OPENSSL31:
# Newer Python returns 'record layer failure'; Python 3.8 on macOS
# returns 'wrong version number' despite OpenSSL >= 3.1.
assert (
'record layer failure' in underlying_error_string
or 'wrong version number' in underlying_error_string
)
elif IS_ABOVE_OPENSSL10:
assert 'wrong version number' in underlying_error_string
else: # pragma: no cover
assert 'unknown protocol' in underlying_error_string


def test_http_over_https_no_data(mocker):
Expand Down
3 changes: 3 additions & 0 deletions docs/changelog-fragments.d/828.contrib.rst
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@webknjaz webknjaz Jun 23, 2026

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Since this patch doesn't fix a bug in Cheroot's runtime, it shouldn't be listed among bugfixes in the change log. Fixing a test is infra work. So it could be a contrib note. Perhaps, a packaging note when we declare that we support new things (like a new Python version, a new OS or a new dep in this case).

Though, feel free to opt out of attaching a change note if it doesn't feel important to surface to the change log audience. You can add the bot:chronographer:skip label and the bot will stop flagging a missing note in the PR.

@julianz- julianz- Jun 23, 2026

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Good points. I changed to a contrib note.

Regarding CPython, I get your idea but it sounds complicated. I was thinking before the issue was the version of OpenSSL but apparently macOS 15 CI runners use Python 3.14.6 with the same bundled OpenSSL 3.6.3 as Windows, but unlike Windows, macOS was already returning the correct record layer failure error. So I have modified the code the check for Windows in addition to the OpenSSL version.

@webknjaz webknjaz Jun 25, 2026

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Could you also symlink this note to 655 and 645, mentioning the prior art/contrib by radez?

@webknjaz webknjaz Jun 25, 2026

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Yeah, it's probably a good idea to normalize these into a unified check where possible. Maybe, migrating to requests in tests over time would be a better solution than trying to rely on low-level stdlib stuff. But this is something to think about separately.

@julianz- julianz- Jun 26, 2026

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I get the intent but wouldn't this make error extraction more complex? requests wraps the SSL error through urllib3, so accessing the underlying message requires a deeper chain than ssl_err.value.args[-1]?

@webknjaz webknjaz Jul 7, 2026

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@julianz- I was mainly thinking of trying to avoid relying on the internals instead. I'm not trilled that the tests are fragile due to the fact that OpenSSL works differently under different runtimes. Technically, this is something external to us and so it'd be a good idea to have it abstracted away, but still something will end up having to normalize the error processing.

Anyway.. Let's postpone this for now.

Original file line number Diff line number Diff line change
@@ -0,0 +1,3 @@
Fixed ``test_https_over_http_error`` failing on Windows with OpenSSL 3.1+,
where the SSL error message is ``wrong version number`` rather than
``record layer failure`` -- by :user:`julianz-`.
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