Why is log output trying to create a directory that already exists?

[timelordx]

Thank you for sharing your solution. This seems to be similar to this issue:

Changing log location

You haven’t shared your systemd unit file for caddy, I’m guessing you have a very restrictive ProtectSystem setting, which is OK, but you haven’t adjusted ReadWritePaths to include your new log directory. Check your systemd settings for Caddy: systemctl show caddy | grep -E 'Protect|ReadWritePaths'