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My School forces me to connect to a server, that does not allow a connection to eg. facebook.com, can I tell the first proxy to connect to a second one, which I set up, that will just connect to facebook.com and forward the result to me. And if this would work, how would I connect to a second proxy in that way?

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  • "Forced" how? Is this a company or institutional computer? Do you have full admin rights?
    – Tetsujin
    Jan 27, 2022 at 16:52
  • After your edit to add "school" I'd give up on this idea. They're not going to let you do that. That's the entire point of having managed computers for schools.
    – Tetsujin
    Jan 27, 2022 at 17:22

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If this is about a proxy server that you must manually set in your browser then yes, this is most likely possible. The basic setup is as follows:

  • A VPN server that accepts TCP connections somewhere (e.g. OpenVPN)
  • A VPN client that can talk to HTTP proxies (again, OpenVPN can do that)
  • Route all internet-bound traffic over VPN (e.g. redirect-gateway def1 in OpenVPN)

For this to work, there are certain requirements:

  • The proxy must not intercept HTTPS traffic (check encrypted sites' certificate chain)
  • The proxy must allow reasonably long-lived connections
  • The proxy must allow using the CONNECT method (required for HTTPS anyway) as well as connecting to your VPN server's port
    • This means the server may have to run on port 443
  • The proxy must allow connecting to the VPN server's host (it is conceivable a school or university proxy would use a list of allowed sites instead of a blocklist)

If this is a transparent proxy (it intercepts traffic to the net, you don't have to set up your browser) this most likely will not work.

If you do not have Administrator access to whatever machine you're using this won't work either.

Don't waste your time at school with Facebook and the like. Do learn how to set this up though, it's valuable knowledge and skill.

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In fact, the idea is good and can work, at least worth a try. The main thing is not to use free proxy servers. Because of your recklessness, the whole central network of the school, along with the data of students, can leak into the network. It would not be very good if this happened. I would advise you to use soax.com proxy servers. I think they are perfect for you. Their price is not too high. I think a high school student could afford a monthly subscription. But the quality and security of these servers are high. In general, be careful. I saw that you have already been offered an effective way to fulfill your idea.I hope my advice does not pass you by.

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