Looking over the commit history for the PR (https://github.com/python/cpython/pull/18239/commits), it looks like that specific Azure Pipelines failure did not start occurring until upstream/master was merged into the PR branch (https://github.com/python/cpython/pull/18239/commits/13d3742fd897e1ea77060547de6d8445877e820e). Therefore, I suspect that the failure is very likely unrelated to the PR; instead either an intermittent failure that was merged into master recently or a possible issue on Azure's end. For now, I'd suggest closing and re-opening the PR again tomorrow to see if the failure still occurs.

Note: I'm also seeing the same exact failure occur in the following separate CPython PRs that were opened recently:

https://github.com/python/cpython/pull/19403
https://github.com/python/cpython/pull/19402
https://github.com/python/cpython/pull/19399

Seeing as it was also occurring in entirely unrelated PRs, it seems to be unrelated to the PEP 585 PR. I'm not seeing a BPO issue for this failure, so I'll open a new one for it.

On Mon, Apr 6, 2020 at 10:24 PM Guido van Rossum <guido@python.org> wrote:
I have a large PR (https://github.com/python/cpython/pull/18239, for PEP 585) that's failing in the Azures pipeline on Win32 and Win64 only. My trusty assistant who has a Windows laptop couldn't reproduce the failure. Can I buy a hint from someone? Steve?

The relevant failure output is:

======================================================================
ERROR: test_load_dll_with_flags (ctypes.test.test_loading.LoaderTest) [WinDLL('_sqlite3.dll', winmode=0)]
----------------------------------------------------------------------
Traceback (most recent call last):
  File "d:\a\1\s\lib\ctypes\test\test_loading.py", line 140, in should_pass
    subprocess.check_output(
  File "d:\a\1\s\lib\subprocess.py", line 420, in check_output
    return run(*popenargs, stdout=PIPE, timeout=timeout, check=True,
  File "d:\a\1\s\lib\subprocess.py", line 524, in run
    raise CalledProcessError(retcode, process.args,
subprocess.CalledProcessError: Command '['d:\\a\\1\\s\\PCbuild\\win32\\python.exe', '-c', "from ctypes import *; import nt;WinDLL('_sqlite3.dll', winmode=0)"]' returned non-zero exit status 1.

----------------------------------------------------------------------


--
--Guido van Rossum (python.org/~guido)
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