I've recreated this bug multiple times on macOS and always with the same result. I'm using Ventura 13.2 on a MacBook Air M1. As far as I can tell the problem seems to affect the following variables in the configuration file: DBW_USER and DBW_BASEURL. The downstream effect of which is making it impossible to log in to the student server with ssh. This can be fixed by running the command as root: sudo dbwebb config or - alternatively - updating the variables manually afterwards. I would suggest that you at least add some information about this to the dbwebb-cli documentation to help others who may be facing this issue.