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test.test_ssl.TestEnumerations is not run when run ssl tests. If add it to the list of test classes it fails:
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ERROR: test_options (test.test_ssl.TestEnumerations)
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Traceback (most recent call last):
 File "/home/serhiy/py/cpython/Lib/test/test_ssl.py", line 4981, in test_options
 enum._test_simple_enum(CheckedOptions, ssl.Options)
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
 File "/home/serhiy/py/cpython/Lib/enum.py", line 1803, in _test_simple_enum
 raise TypeError('enum mismatch:\n %s' % '\n '.join(failed))
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
TypeError: enum mismatch:
 '_use_args_':
 checked -> False
 simple -> True
 '__format__': checked -> <function Enum.__format__ at 0x7f18691815a0> simple -> <function IntFlag.__format__ at 0x7f1869182620>
 '__getnewargs__': checked -> None simple -> <method '__getnewargs__' of 'int' objects>
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ERROR: test_sslerrornumber (test.test_ssl.TestEnumerations)
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Traceback (most recent call last):
 File "/home/serhiy/py/cpython/Lib/test/test_ssl.py", line 4998, in test_sslerrornumber
 enum._test_simple_enum(Checked_SSLMethod, ssl._SSLMethod)
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
 File "/home/serhiy/py/cpython/Lib/enum.py", line 1803, in _test_simple_enum
 raise TypeError('enum mismatch:\n %s' % '\n '.join(failed))
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
TypeError: enum mismatch:
 extra key: 'PROTOCOL_SSLv23'
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ERROR: test_sslmethod (test.test_ssl.TestEnumerations)
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Traceback (most recent call last):
 File "/home/serhiy/py/cpython/Lib/test/test_ssl.py", line 4973, in test_sslmethod
 enum._test_simple_enum(Checked_SSLMethod, ssl._SSLMethod)
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
 File "/home/serhiy/py/cpython/Lib/enum.py", line 1803, in _test_simple_enum
 raise TypeError('enum mismatch:\n %s' % '\n '.join(failed))
 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
TypeError: enum mismatch:
 extra key: 'PROTOCOL_SSLv23'
======================================================================
ERROR: test_verifyflags (test.test_ssl.TestEnumerations)
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Traceback (most recent call last):
 File "/home/serhiy/py/cpython/Lib/test/test_ssl.py", line 5002, in test_verifyflags
 enum.FlagEnum, 'VerifyFlags', 'ssl',
 ^^^^^^^^^^^^^
AttributeError: module 'enum' has no attribute 'FlagEnum'
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Looks like `TestEnumerations` was never added to `tests` in `test_main`. https://github.com/python/cpython/commit/a02cb474f9c097c83cd444a47e9fb5f99b4aaf45#diff-d526ded1c360bed6b222de46f4ca92b834f978ebed992fb3189bf9a94a198578R4702
I will try to enable it and fix failures.

New changeset d897579a80da3f4572d96501c41bec6cacb10d84 by Nikita Sobolev in branch 'main':
bpo-45185: enables `TestEnumerations` in `test_ssl` (GH-28330)
https://github.com/python/cpython/commit/d897579a80da3f4572d96501c41bec6cacb10d84

Thank you Nikita!
The test was added in issue38659 and was not backported, so it is 3.11 only issue.