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Say Alice wants to open up an HTTPS connection to Bob through a proxy named Earl.

What prevents Earl from reading alices request, opening a connection pretending to be bob, and then opening a https connection with bob pretending to be Alice , and snooping on the traffic as it passes through ?

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[-] IAm_A_Complete_Idiot@sh.itjust.works 2 points 1 year ago* (last edited 1 year ago)

This is about PKI. An HTTPS server has a TLS cert, and that TLS cert is signed by / created by a certificate authority (or CA). When you connect to a service over HTTPS, a TLS handshake happens. The handshake starts by the client asking a server to setup a session, and the server hands back it's certificate. This certificate can be used to encrypt traffic, but not decrypt it. The client makes sure the certificate is signed by a CA it trusts (such as let's encrypt).

Once the client has this certificate, it sends a key to the server in encrypted form, and the server decrypts it. They both now use this key to communicate.

The MITM server can't compromise the session because: If it swaps the certificate (or in other words, the encryption key the server sent), that key won't be trusted because it isn't signed by a CA the client trusts.

If the MITM tries to send its own shared key signed by the servers certificate - it doesn't really matter since it can't read the clients messages anyways to get the shared key from the client. If it forwards it, then you effectively have two separate https sessions with their own keys, and the server will treat them as distinct.

this post was submitted on 18 Oct 2023
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