Using my raspberry pi, I created a pptp vpn server, but I find myself unable to connect to it under my school's wifi (I am able to connect to other wifi via the raspberry pi). Would programs such as iprism the school is running prevent me from accessing the vpn?
Yes iprism could prevent you from connecting to your PPTP server as any other webfilter, proxy server, etc. could do as well.
You maybe get around that if you're dropping PPTP and use OpenVPN instead. This alone wouldn't help much but running your server on port 443 could do the trick .
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