Bypassing school SSL inspection

Hello!

Our school implemented an SSL inspection tool called ContentKeeper. It’s super annoying. Im currently running ubuntu on a USB stick at school as the laptops there don’t even allow us to install python (which I have a class for)

Normally all requests go through as expected when using a laptop without my own OS, but whenever I try to use mine I get a MITM warning that I can’t ignore. Absolutely no connections are making it through to shadowsocks or any sort of proxy server on both my home PC or a hosted server.

Also I cannot make any connection with SSH from the school network

Here are some things I have tried:

Shadowsocks: Nope no connection at all on ports 80, 443 or default?? Theres a small chance that i messed up something but im also not even able to ssh into my pc or my server from the school internet on my ubuntu stick

Remoting into my home PC is an option but the basic things I have tried (chrome remote desktop, parsec, steam remote play) all do not have internet access.

Tor: Nope

OpenVPN ports 80, 443: Nope 🙁

DNS tunnel (I cant find any decent tutorial and I keep seeing everywhere that it slows connection; I need a fast connection ideally for remote desktop with low latency): Havent tried

I do have connection from my IOS and Android device when I connect to a free VPN (XVPN) however installing it on the laptop makes it not work for some reason (Have tried many VPNS)

Sorry for the massive block of text. Also please go easy on me because I am slightly newer to networking! 🙂

I will update the post with things I have tried and will respond to every comment with advice.

Thank you in advance!

submitted by /u/DinnerFew9941
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