Hi everyone, I’ve been trying to understand how MiTM setups like a transparent proxy work.

Obviously, the use-case here is in a personal scope: I’d like to inspect the traffic of some of my machines. I am aware that Squid can be a transparent proxy, and some might use the Burp Suite to analyse network traffic.

Could someone explain the basic networking and the concept of certificates in this scenario? I feel like I don’t understand how certificates are used well enough.

For example: I realise that if someone inserts a root certificate in the certificate store of an OS, the machine trusts said CA, thus allowing encrypted traffic from the machine to be decrypted. However, say the machine was trying to access Amazon; won’t Amazon have its own certificate? I don’t know how I’m confused about such a simple matter. Would really appreciate your help!

  • surewhynotlem@lemmy.worldEnglish
    5·
    11 months ago

    If you are acting as the proxy for the user, then all web requests go through you. A normal proxy would just forward those on to the Amazon (e.g.) server.

    In your scenario, the proxy sends a cert to the client saying ‘I’m Amazon’, and the client believes it. The client talks to you like you’re Amazon, and you read all his messages. At the same time, you talk to Amazon pretending to be the user, so you can get all the correct Amazon responses to send back to the user.

    • MigratingtoLemmy@lemmy.worldOPEnglish
      1·
      11 months ago

      the proxy sends a cert to the client saying ‘I’m Amazon’, and the client believes it

      Thanks, could you explain this a bit more? I didn’t understand what you mean by “sends a cert saying ‘I’m Amazon’”

      • Monkey With A Shell@lemmy.socdojo.comEnglish
        3·
        11 months ago

        A decrypting proxy acts like a local certificate authority and issues a certificate on behalf of the site to create one encrypted connection between the client and proxy while creating a second on with the original site on the other side.

        The client will get an error (or depending on the site and browser may refuse to connect at all in the case of pinned and preloaded certificates) indicating that they’re connecting to a site with a certificate from an untrusted issued unless they’ve been configured to trust the CA held on the proxy.

        The ‘break’ between the client side connection and the server side connection will be in plaintext and can be examined through internal tools or sent to external ones typically through ICAP.

        • MigratingtoLemmy@lemmy.worldOPEnglish
          1·
          11 months ago

          I see. Which would mean that in cases where the application/OS can be made to blindly trust the “fake” CA (by inserting a root certificate into the certificate store, like in Android), the proxy can simply send the certificate and the client will believe that the certificate comes from Amazon. The certificate list can be refreshed by flushing the cache, yes?

          Thanks for the explanation

          • stifle867@programming.devEnglish
            1·
            11 months ago

            There are some cases where this would not work by the way. It’s called certificate pinning and it’s basically when an application comes with the trusted certificate for a host built-in. Even if you were to override it with a root certificate in the certificate store, the app simply wouldn’t use it.

      • SheeEttin@lemmy.worldEnglish
        2·
        11 months ago

        That’s literally it. It sends a cert for amazon.com, that your client trusts, because the CA cert used to sign it is in your trusted store.

        • MigratingtoLemmy@lemmy.worldOPEnglish
          1·
          11 months ago

          I see, thanks for the explanation. Amazon sends the certificate to the proxy, and the proxy sends its own certificate, masquerading as amazon, to the user.

          Thanks

          • canni@lemmy.oneEnglish
            2·
            11 months ago

            I think it’s important to understand how a typical SSL certificate is generated. Basically, there are a handful of companies that we have all agreeded to trust. When you download Chrome it comes with a set of trusted root certificates, so does your OS, etc. So when Amazon wants to create an SSL for amazon.com, the only way they can do that is by contacting one of those handful of trusted companies and getting them to issue a certificate that’s says Amazon.com. When you go to the site, you see a trusted party generated the cert and your browser is happy.

            When you create a new root certificate and install it on your computer, you become one of those companies. So now, you can intercept traffic, decrypt it, read it, reissue a certificate for amazon.com (the same way Amazon would have gotten one from the third parties), reencrypt it, and pass it along to the client. Because the client trusts you it’s still a valid certificate. But if you inspect the certificate on the client side the root signer will no longer be GoDaddy or whatever, it will be you.

            • MigratingtoLemmy@lemmy.worldOPEnglish
              1·
              11 months ago

              Basically, if I were to run a CA locally (on my network) and use that certificate in some OS, I should be able to set up a MiTM setup easily. Except that applications like web browsers don’t care and will utilise certificate pinning anyway, regardless of which certificates I keep in my certificate store in the OS.

              Also, let’s say I’m running HAProxy/Caddy/NGINX at home which acts as my SSL-termination point for my network. In this case, if a service wants to access the internet, do these reverse proxies encrypt the outbound traffic with a different certificate?

              • canni@lemmy.oneEnglish
                2·
                11 months ago

                If I understand the question, the traffic in your local intranet will basically always be encrypted with your root cert. So client -> proxy with your cert, then normal internet encryption from proxy -> internet.

                For the apps, it depends on the app, but you can usually insert your cert into their store, it might just be different than the systems store. This could be hard to do on an non-rooted iPhone, idk. My experience is with Linux desktops. For example, in chromium based apps, there is a database in ~/.pki/nssdb that you can insert your cert into. Again, this is something I do at work where we have a very tightly controlled network and application stack. I would not recommend a MiTM proxy for your home environment, it will only cause headaches.

                • MigratingtoLemmy@lemmy.worldOPEnglish
                  1·
                  11 months ago

                  Ah, I see. I suppose I got a bit confused, and wanted to confirm how encryption would work for outbound traffic. Just to be sure: when an application wants to send encrypted data to a website/service on the Internet, it will use the respective certificate for said website. However, if one runs a transparent proxy in the middle and inserts a root certificate in the certificate store of the application, said certificate becomes valid (and the de-facto pick) for all websites, and this is what the client begins to use for everything.

                  Is that how it works?