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Problem Background:

As part of the Computer Networking course assignment, I have been given task of implementing a Proxy Server ( using python socket and ssl module ) that handles https communications between the browser and the origin server (The real server that my browser wants to talk to).

What I have done so far:

I have implemented the above requirement using ssl sockets and also generated self-signed 'cert.pem' 'key.pem' files.

What I need to do:

Now I just need to tell my browser (chrome 89 on kubuntu 20.04) to accept this self-signed certificate and then test the working of my proxy server.

Reading from this stackoverflow question, I can see that I have to: (1) become my own CA (2) then sign my SSL certificate as a CA. (3) Then import the CA certificate (not the SSL certificate, which goes onto my server) into Chrome.

My confusion/question:

So if I do this, when eventually I am done with this assignment, how do I reverse all these steps to get my browser in the previous state before I had made all these changes. Also, how to reverse the "become your own CA" and also delete the SSL certificates signed by my CA. Basically, I want my system to return to the previous state it was before I would have made all these changes.

UPDATE:

I have done the previously outlined steps but now I get an error.

Here is a snippet of my code:

serv_socket = socket(AF_INET, SOCK_STREAM)
serv_socket.bind(('', serv_port))
serv_socket.setsockopt(SOL_SOCKET, SO_REUSEADDR, 1)

context = ssl.create_default_context(ssl.Purpose.CLIENT_AUTH)
context = context.load_cert_chain('cert.pem', 'key.pem')
context.set_ciphers('EECDH+AESGCM:EDH+AESGCM:AES256+EECDH:AES256+EDH')

serv_socket.listen(10)

socket_to_browser, addr = serv_socket.accept()

conn_socket_to_browser = context.wrap_socket(socket_to_browser, server_side=True)

At the last line conn_socket_to_browser = context.wrap_socket(socket_to_browser, server_side=True) an exception is thrown: [SSL: HTTPS_PROXY_REQUEST] https proxy request (_ssl.c:1123)

What am I doing wrong ?

Mehran Kamal
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1 Answers1

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As glamorous as "becoming your own CA" sounds, with openssl it basically comes down to creating a self-signed certificate, and then creating a directory where some CA-specific configuration will be stored (I don't fully remember the specifics, but I think it was just some files related to CNs and serial numbers) so basically reversing the "become your own CA" step is something as mundane as deleting this directory along with the private key and self-signed certificate you were using for the CA. That's it, the CA is no more.

And for chrome returning to the previous state, you would just go the the CA list where you added the CA certificate, select it and delete it. Chrome will stop accepting certificates signed by your CA.

Regarding your new problem... In my opinion, you have developed some kind of reverse proxy (meaning that you expect normal HTTPS requests that you then redirect to the real server) but you have configured Chrome to use it as a forward proxy. In this case, Chrome does not send it a normal HTTPS request, it sends a special non-encrypted CONNECT command and only after receiving the non-encrypted response, it negotiates the TLS connection. That's why openssl says "https proxy request" because it has detected a "https proxy request" (a CONNECT command) instead of the normal TLS negotiation.

You can take a look at How can a Python proxy server (using SSL socket) pretend to be an HTTPS server and specify my own keys to get decrypted data?

It's python, but I think that you'll get the idea

Ion Larrañaga
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