example:https://github.com/python/cpython/pull/19073/checks?check_run_id=519539592I suggest to not to add information for os.getgrouplistif the OSError is raised.

or adding <OSError> might be great just like getpwuid

These errors are really strange.Steve Dower: are you aware of anything recent change on the macOS job of Azure Pipelines / GH Actions.pythoninfo:---os.uname: posix.uname_result(sysname='Darwin', nodename='Mac-1422.local', release='19.3.0', version='Darwin Kernel Version 19.3.0: Thu Jan  9 20:58:23 PST 2020; root:xnu-6153.81.5~1/RELEASE_X86_64', machine='x86_64')platform.architecture: 64bitplatform.platform: macOS-10.15.3-x86_64-i386-64bit---> example:https://github.com/python/cpython/pull/19073/checks?check_run_id=519539592./python.exe -m test.pythoninfoERROR: collect_pwd() failedTraceback (most recent call last):  File "/Users/runner/runners/2.165.2/work/cpython/cpython/Lib/test/pythoninfo.py", line 761, in collect_info    collect_func(info_add)  File "/Users/runner/runners/2.165.2/work/cpython/cpython/Lib/test/pythoninfo.py", line 336, in collect_pwd    groups = os.getgrouplist(entry.pw_name, entry.pw_gid)OSError: [Errno 0] ErrorCollection failed: exit with error>PR 19075test_posix.test_getgrouplist() failed with:======================================================================ERROR: test_getgrouplist (test.test_posix.PosixTester)----------------------------------------------------------------------Traceback (most recent call last):  File "/Users/runner/runners/2.165.2/work/cpython/cpython/Lib/test/test_posix.py", line 1028, in test_getgrouplist    self.assertIn(group, posix.getgrouplist(user, group))OSError: [Errno 25] Inappropriate ioctl for device

This error has to do with the number of groups a particular user is associated with. We’ve squashed similar bugs in the past but it looks like something has changed again in recent releases of macOS. It’s not Azure specific.

tl; dr os.getgrouplist() is limited to 17 groups and fails with a random OSError if the request user has more groups.PR 19118 fix the issue.--On macOS-10.15.1-x86_64-i386-64bit (python -m platform), os.getgrouplist() fails with my user name and group identifier:>>> os.getgrouplist('haypo', 20)Traceback (most recent call last):  File "<stdin>", line 1, in <module>OSError: [Errno 0] ErrorFull example:macbook:master haypo$ ./python.exe Python 3.9.0a4+ (heads/master:da2914d, Mar 20 2020, 09:45:36) [Clang 11.0.0 (clang-1100.0.33.8)] on darwinType "help", "copyright", "credits" or "license" for more information.>>> import os, pwd>>> entry=pwd.getpwuid(os.getuid())>>> os.getgrouplist(entry.pw_name, entry.pw_gid)Traceback (most recent call last):  File "<stdin>", line 1, in <module>InterruptedError: [Errno 4] Interrupted system call>>> os.getgrouplist(entry.pw_name, entry.pw_gid)Traceback (most recent call last):  File "<stdin>", line 1, in <module>OSError: [Errno 0] Error>>> entrypwd.struct_passwd(pw_name='haypo', pw_passwd='********', pw_uid=502, pw_gid=20, pw_gecos='Victor Stinner', pw_dir='/Users/haypo', pw_shell='/bin/bash')My user has the following groups:macbook:master haypo$ iduid=502(haypo) gid=20(staff) groups=20(staff),702(com.apple.sharepoint.group.2),12(everyone),61(localaccounts),79(_appserverusr),80(admin),81(_appserveradm),98(_lpadmin),701(com.apple.sharepoint.group.1),33(_appstore),100(_lpoperator),204(_developer),250(_analyticsusers),395(com.apple.access_ftp),398(com.apple.access_screensharing),399(com.apple.access_ssh),400(com.apple.access_remote_ae),703(com.apple.sharepoint.group.3)My user has 18 groups.MAX_GROUPS=16, Python uses 1 + MAX_GROUPS.getgrouplist() manual page says:RETURN VALUES     The getgrouplist() function returns 0 on success.  If the size of the group list is too small to hold     all the user's groups, getgrouplist() returns -1 to indicate failure.  In this case, the group array     will be filled with as many groups as will fit.In short, getgrouplist() doesn't set errno on failure.

Python 3.7 and 3.8 are also affected on macOS 10.15 (Catalina).

Thanks for the PR, Victor, it does address the problem.  I went back and explicitly tested on macOS 10.14 and 10.13 by creating some more groups and adding the user to them and the same failure occurred there so this is not just a 10.15 issue.  Most likely this hasn't been an issue before is that 10.15 creates more groups for system services than the earlier versions did.  So the PR should be updated to remove the 10.15 (and 10.5!) references.

> Most likely this hasn't been an issue before is that 10.15 creates more groups for system services than the earlier versions did.Aha, interesting. I updated my PR to remove mentions of the macOS version number. I just wrote "on macOS". Yeah, I wouldn't be surprised that the function always failed.--I'm not sure that the Linux implementation is correct. It rely on errno, whereas Linux manual page of getgrouplist() doesn't say anything about errno being set on error.Moreover, on Linux, getgrouplist() can also fail with -1 if the group list is too small. In that case, ngroups is updated to the number of groups and so can be used to enlarge the list!

test.pythoninfo of the macOS job on the PR:os.getgrouplist: 20, 0, 12, 61, 79, 80, 81, 98, 264, 399, 701, 33, 100, 204, 250, 395, 398, 400os.getgroups: 20, 0, 12, 61, 79, 80, 81, 98, 264, 399, 701, 33, 100, 204, 250, 395, 398, 400So yeah, there are 18 groups ;-)

New changeset8ec7370c89aa522602eb9604086ce9f09770953d by Victor Stinner in branch 'master':bpo-40014: Fix os.getgrouplist() on macOS (GH-19118)https://github.com/python/cpython/commit/8ec7370c89aa522602eb9604086ce9f09770953d

New changeset21bee0bd71e1ad270274499f9f58194ebb52e236 by Miss Islington (bot) in branch '3.8':bpo-40014: Fix os.getgrouplist() on macOS (GH-19118)https://github.com/python/cpython/commit/21bee0bd71e1ad270274499f9f58194ebb52e236

New changeset1cdc61c7673f71f2cef57715e482c84efda6d9e0 by Miss Islington (bot) in branch '3.7':bpo-40014: Fix os.getgrouplist() on macOS (GH-19118)https://github.com/python/cpython/commit/1cdc61c7673f71f2cef57715e482c84efda6d9e0

> Moreover, on Linux, getgrouplist() can also fail with -1 if the group list is too small. In that case, ngroups is updated to the number of groups and so can be used to enlarge the list!I tested by manually initializing ngroups to a value way lower than MAX_GROUPS (65536 on my Fedora 31): os.getgrouplist() raises OSError() with a random errno, getgrouplist() doesn't set errno on failure.I wrotePR 19126 to fix the issue on all platforms. The glibc implementation is detected and used: use updated ngroups value (only if it's larger).

New changesetf5c7cabb2be4e42a5975ba8aac8bb458c8d9d6d7 by Victor Stinner in branch 'master':bpo-40014: Fix os.getgrouplist() (GH-19126)https://github.com/python/cpython/commit/f5c7cabb2be4e42a5975ba8aac8bb458c8d9d6d7

New changeset5753fc69977bd9f70ecb4d466bda650efccf9e0a by Miss Islington (bot) in branch '3.7':bpo-40014: Fix os.getgrouplist() (GH-19126)https://github.com/python/cpython/commit/5753fc69977bd9f70ecb4d466bda650efccf9e0a

New changesetaf6fd1faa68f57c11c862624798f8510b7cac68a by Miss Islington (bot) in branch '3.8':bpo-40014: Fix os.getgrouplist() (GH-19126)https://github.com/python/cpython/commit/af6fd1faa68f57c11c862624798f8510b7cac68a

Ned: so Linux was also impacted, but Linux only has an issue with more than 65536 groups :-D macOS MAX_GROUPS is now only 16 (Python uses MAX_GROUPS+1)! Maybe MAX_GROUPS was reduced recently. I'm not sure.Anyway, os.getgrouplist() does no longer depend on MAX_GROUPS hardcoded limit, but grow the group list dynamically. It should now work with any number of groups an all platforms (which provide the getgrouplist() function ;-)) on Python 3.7, 3.8 and master branches.Thanks Dong-hee Na for the bug report and your PR.