Can you post the list of modules that you have loaded plus your full httpd config (maybe you can upload them to the bug report)? Another think to try would be to use gdb and http -X to trace one process, but it might be overkill. You could also try to add trace-log specific prints in the httpd .c files where Last-Modified is changed to see if anything comes up, but again it might be very time consuming.I tried to repro on 2.4.20 but I wasn't able, so I took a look to https://www.apache.org/dist/httpd/CHANGES_2.4 to see if it was something corrected with 2.4.13 but I didn't see anything obvious. You also mentioned that there seem to be no distro specific patches applied to the httpd package, so the issue might be really difficult to track.Will try to check you docker image during the next days, maybe we can come up with something. In the meantime, is there any possibility to switch to a different httpd version (that works) to unblock you?Luca