

It’s likely illegal. The administration would call it theft of service because it’s not authorized and they wouldn’t be wrong. I also don’t see why you would want to do it. You’re giving the IT department at your school complete access to your web history.
The biggest issue I have with Caddy and running ancillary services as some services attempt to utilize port 80 and/or 443 (and may not be configurable), which of course isn’t possible because Caddy monopolizes those ports. The best solution to this I’ve found is to migrate Caddy and my services to docker containers and adding them all to the same “caddy” network.
With your caddy instance still monopolizing port 80 and 443, you can use the Docker
expose
orport
parameters to allow your containers to utilize port 80 and/or 443 from within the container, but proxify it on the host network. This is what my caddy config looks like;It works very well.