Found one condition where the assertion failure happens. The test case I have 
does this:

sock = socket.create_connection((host, int(env.https_port)))
try:
    sock.settimeout(0.5)
    sock.recv(1024)
    assert False
except Exception as ex:
    print(f"as expected: {ex}")
sock.close()

Which is all that's needed to trigger the assertion. The server is not stopped.

The log for this thread only gives:
[Tue Jul 13 13:51:29.476747 2021] [mpm_event:trace4] [pid 31582:tid 
123145480441856] event.c(858): [client 127.0.0.1:51768] lingering close in 
state 5
[Tue Jul 13 13:51:29.476769 2021] [mpm_event:trace4] [pid 31582:tid 
123145480441856] event.c(833): [remote 127.0.0.1:51768] kill connection in 
state 5
[Tue Jul 13 13:51:29.476775 2021] [mpm_event:trace4] [pid 31582:tid 
123145480441856] event.c(563): closing socket -1/7fa24681d0b0 from 
process_socket
[Tue Jul 13 13:51:29.476779 2021] [mpm_event:error] [pid 31582:tid 
123145480441856] (9)Bad file descriptor: AH00468: error closing socket 
-1/7fa24681d0b0 from process_socket
[Tue Jul 13 13:51:29.476799 2021] [core:crit] [pid 31582:tid 123145480441856] 
AH00102: [Tue Jul 13 13:51:29 2021] file event.c, line 569, assertion "0" failed

I added a trace4 "closing socket" before the apr_socket_close(), grepping for 
that in the log shows:
[Tue Jul 13 13:51:28.467677 2021] [mpm_event:trace4] [pid 31582:tid 
123145479905280] event.c(563): closing socket 15/7fa24681d0a0 from 
process_lingering_close
[Tue Jul 13 13:51:29.476775 2021] [mpm_event:trace4] [pid 31582:tid 
123145480441856] event.c(563): closing socket -1/7fa24681d0b0 from 
process_socket
[Tue Jul 13 13:51:29.476779 2021] [mpm_event:error] [pid 31582:tid 
123145480441856] (9)Bad file descriptor: AH00468: error closing socket 
-1/7fa24681d0b0 from process_socket
[Tue Jul 13 13:51:29.984132 2021] [mpm_event:trace4] [pid 31584:tid 
123145470783488] event.c(563): closing socket -1/7fa24681f0b0 from 
process_socket
[Tue Jul 13 13:51:29.984138 2021] [mpm_event:error] [pid 31584:tid 
123145470783488] (9)Bad file descriptor: AH00468: error closing socket 
-1/7fa24681f0b0 from process_socket



Thread 21 Crashed:
0   libsystem_kernel.dylib              0x00007fff202e292e __pthread_kill + 10
1   libsystem_pthread.dylib             0x00007fff203115bd pthread_kill + 263
2   libsystem_c.dylib                   0x00007fff202664ab __abort + 139
3   libsystem_c.dylib                   0x00007fff20266420 abort + 135
4   httpd                               0x000000010dbfdb72 ap_log_assert + 130 
(log.c:1649)
5   mod_mpm_event.so                    0x000000010e5154bf 
close_socket_nonblocking_ex + 223 (event.c:569)
6   mod_mpm_event.so                    0x000000010e515158 kill_connection_ex + 
67 (event.c:835) [inlined]
7   mod_mpm_event.so                    0x000000010e515158 
start_lingering_close_blocking_ex + 184 (event.c:862)
8   mod_mpm_event.so                    0x000000010e514da9 process_socket + 
1289 (event.c:1261)
9   mod_mpm_event.so                    0x000000010e514769 worker_thread + 809 
(event.c:2394)
10  libapr-1.0.dylib                    0x000000010ddb9341 dummy_worker + 17 
(thread.c:147)
11  libsystem_pthread.dylib             0x00007fff203118fc _pthread_start + 224
12  libsystem_pthread.dylib             0x00007fff2030d443 thread_start + 15



- Stefan

> Am 13.07.2021 um 12:39 schrieb Stefan Eissing <stefan.eiss...@greenbytes.de>:
> 
> Coming back to this: I vote for applying this to trunk. On a fresh setup, I 
> do not see and assert failures in my test.
> 
> - Stefan
> 
>> Am 08.07.2021 um 20:17 schrieb Yann Ylavic <ylavic....@gmail.com>:
>> 
>> On Thu, Jul 8, 2021 at 4:21 PM Stefan Eissing
>> <stefan.eiss...@greenbytes.de> wrote:
>>> 
>>> I see many of those:
>>> [Thu Jul 08 14:16:55.301670 2021] [mpm_event:error] [pid 81101:tid 
>>> 123145411510272] (9)Bad file descriptor: AH00468: error closing socket 
>>> -1/7ff9cf0086b0 from process_socket
>>> 
>>> which come from event.c#1263: rc = start_lingering_close_blocking(cs);
>>> calling event.c#864: kill_connection_ex(cs, from);
>>> and event.c#837: close_socket_nonblocking_ex(cs->pfd.desc.s, from);
>> 
>> OK, so I think this could be addressed by the attached patch.
>> This is the same as v0 plus some changes in ap_start_lingering_close()
>> (from server/connection.c) to not close the socket on error.
>> ap_start_lingering_close() did not close the socket consistently, so
>> the caller had to call apr_socket_close() anyway and sometimes fail..
>> The close on failure is moved to ap_lingering_close() which is the one
>> that should care.
>> 
>> Still the AP_DEBUG_ASSERT(0) triggering with this?
>> <event_ka_no_lingerv3.diff>
> 

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