Extract of cpython-testlogging.log:

0:08:58 [198/404] test_logging
--- Logging error ---
Traceback (most recent call last):
  File "/mnt/d/Share/source/cpython-master/Lib/logging/handlers.py", line 634, in emit
    self.send(s)
  File "/mnt/d/Share/source/cpython-master/Lib/logging/handlers.py", line 692, in send
    self.sock.sendto(s, self.address)
OSError: [Errno 22] Invalid argument
Call stack:
  File "/mnt/d/Share/source/cpython-master/Lib/runpy.py", line 193, in _run_module_as_main
    "__main__", mod_spec)
  File "/mnt/d/Share/source/cpython-master/Lib/runpy.py", line 85, in _run_code
    exec(code, run_globals)
  File "/mnt/d/Share/source/cpython-master/Lib/test/regrtest.py", line 50, in <module>
    _main()
  File "/mnt/d/Share/source/cpython-master/Lib/test/regrtest.py", line 46, in _main
    main()
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/main.py", line 532, in main
    Regrtest().main(tests=tests, **kwargs)
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/main.py", line 468, in main
    self._main(tests, kwargs)
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/main.py", line 490, in _main
    self.run_tests()
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/main.py", line 418, in run_tests
    self.run_tests_sequential()
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/main.py", line 343, in run_tests_sequential
    result = runtest(self.ns, test)
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/runtest.py", line 129, in runtest
    result = runtest_inner(ns, test, display_failure=not ns.verbose)
  File "/mnt/d/Share/source/cpython-master/Lib/test/libregrtest/runtest.py", line 165, in runtest_inner
    test_runner()
  File "/mnt/d/Share/source/cpython-master/Lib/test/support/__init__.py", line 1576, in inner
    return func(*args, **kwds)
  File "/mnt/d/Share/source/cpython-master/Lib/test/test_logging.py", line 4334, in test_main
    support.run_unittest(*tests)
  File "/mnt/d/Share/source/cpython-master/Lib/test/support/__init__.py", line 1909, in run_unittest
    _run_suite(suite)
  File "/mnt/d/Share/source/cpython-master/Lib/test/support/__init__.py", line 1875, in _run_suite
    result = runner.run(suite)
  File "/mnt/d/Share/source/cpython-master/Lib/test/support/__init__.py", line 1751, in run
    test(result)
  File "/mnt/d/Share/source/cpython-master/Lib/unittest/suite.py", line 84, in __call__
    return self.run(*args, **kwds)
  File "/mnt/d/Share/source/cpython-master/Lib/unittest/suite.py", line 122, in run
    test(result)
  File "/mnt/d/Share/source/cpython-master/Lib/unittest/suite.py", line 84, in __call__
    return self.run(*args, **kwds)
  File "/mnt/d/Share/source/cpython-master/Lib/unittest/suite.py", line 122, in run
    test(result)
  File "/mnt/d/Share/source/cpython-master/Lib/unittest/case.py", line 649, in __call__
    return self.run(*args, **kwds)
  File "/mnt/d/Share/source/cpython-master/Lib/unittest/case.py", line 601, in run
    testMethod()
  File "/mnt/d/Share/source/cpython-master/Lib/test/test_logging.py", line 1580, in test_output
    logger.error("spam")
Message: 'spam'
Arguments: ()
^C
Test suite interrupted by signal SIGINT.


I'm watching closely Windows buildbots for 2 years, and I don't recall having seen this error recently. So I close the issue as "out of date".