Hi Graham, Stunnel does not implement automatic log rotation and it will not overwrite earlier log entries. It will always try to append new entries at the end. By default, the log file is named stunnel.log. If you run out of storage, stunnel will probably crash. In Unix-like OSes like Linux or FreeBSD, you can configure OS tasks to gracefully handle the log management. Periodically the stunnel server process is stopped, the oldest log file is deleted and/or compressed and the newest/current log is renamed. Then stunnel is started and a new stunnel log is created. In Windows you could do something similar by creating a suitable script or batch file and running it via Task Scheduler. Regards Jose On Sunday, May 31, 2026 at 01:26:22 AM GMT-5, Graham Jones via stunnel-users <stunnel-users@lists.stunnel.org> wrote: I'm new to Stunnel. stunnel 5.78 on x64-pc-mingw32-gnu platform Windows 7 Pro. I see the option to "Show Log Window". I have read the manual. I see there is an option to specify an output file; I am not using this option. My question: When the space allocated to the log information fills up, what happens? Does stunnel overwrite the oldest log entries first? Or does it crash? Regards, == Graham _______________________________________________ stunnel-users mailing list -- stunnel-users@lists.stunnel.org To unsubscribe send an email to stunnel-users-leave@lists.stunnel.org