Netgate Discussion Forum
    • Categories
    • Recent
    • Tags
    • Popular
    • Users
    • Search
    • Register
    • Login

    Squid-3.5.27 SSL Custom works few minutes. MITM breakdown

    Scheduled Pinned Locked Moved Cache/Proxy
    13 Posts 3 Posters 1.7k Views
    Loading More Posts
    • Oldest to Newest
    • Newest to Oldest
    • Most Votes
    Reply
    • Reply as topic
    Log in to reply
    This topic has been deleted. Only users with topic management privileges can see it.
    • D
      denisk
      last edited by

      Good day!
      I'm using 2.4.3-RELEASE-p1and Squid-3.5.27 with configuration below.
      0_1535010965442_s1.jpeg
      0_1535010976925_s2.jpeg
      0_1535010992182_s3.jpeg
      0_1535011001456_s4.jpeg
      0_1535011021050_s5.jpeg
      0_1535011036432_s6.jpeg
      0_1535011080822_s7.jpeg
      Certificate, which used by Squid installed to Chrome and Firefox as Root Trusted.
      And this configuration work only few minutes (~15-20) with traffic intensity, which presented below.
      0_1535011125365_s8.jpeg
      And after 15-20 minutes I see error in Chrome
      0_1535011178805_chrome_alt_subj_pic1.png
      I don't understand reason of this behaviour.
      Squid doesn't show any anomalies in logs.
      pfSense has:

      • CPU Type Intel(R) Xeon(R) CPU X5650 @ 2.67GHz 4 CPUs: 4 package(s)
      • 8 Gb RAM
      • 150 Gb HDD
      1 Reply Last reply Reply Quote 0
      • P
        pfsensation
        last edited by

        Have you installed the CA certificate on the client device?

        D 1 Reply Last reply Reply Quote 0
        • D
          denisk @pfsensation
          last edited by

          @pfsensation
          Of course installed. This configuration work few minutes - I see myself certificate in Chrome

          P 1 Reply Last reply Reply Quote 0
          • P
            pfsensation @denisk
            last edited by

            @denisk said in Squid-3.5.27 SSL Custom works few minutes. MITM breakdown:

            @pfsensation
            Of course installed. This configuration work few minutes - I see myself certificate in Chrome

            Can you check the cert on the warning message for me? I believe this is one of the reasons I gave up on Squid and permanently moved to E2 Guardian. Chrome requires that the certificate includes a SAN (Subject Alternative name) instead of a common name. My guess is that the bug I experienced still exists and that Squid is not generating the fake cert correctly with the SAN.

            D 1 Reply Last reply Reply Quote 0
            • D
              denisk @pfsensation
              last edited by

              @pfsensation 0_1535022151860_BEB18B45-1FF7-4C60-8F9A-445160477C0F.jpeg

              1 Reply Last reply Reply Quote 0
              • P
                pfsensation
                last edited by

                Chrome should be easiest, click on the "not secure" box near the URL. Then click certificate, it should open the certificate up. Check on the details tab at the top of the window and see if the certificate contains a valid Subject Alternative Name.

                1 Reply Last reply Reply Quote 0
                • D
                  denisk
                  last edited by

                  @pfsensation said in Squid-3.5.27 SSL Custom works few minutes. MITM breakdown:

                  Subject Alternative Name

                  Yes, I see the problem with Subject Alternative Name.
                  For example, website was yandex.ru:
                  0_1535085712077_s9.jpeg
                  On this picture I see, what connection is secured (#1), and such certificate signed by my certificate (#2 - internal-ca), and there valid Subject Alternative Name (#3).

                  After 15 minutes next picture:
                  0_1535085528066_s10.jpeg
                  Connection is NOT secured (#4), yandex's certificate also signed by my certificate (#5), BUT Subject Alternative Name is IP address (#6).

                  For additional information, such problem appears with other websites:
                  0_1535085943327_s11.jpeg

                  But why such problem appears through few minutes? On another object, where are the same pfSense instance, such problem doesn't appear!

                  P 1 Reply Last reply Reply Quote 0
                  • P
                    pfsensation @denisk
                    last edited by pfsensation

                    @denisk To be honest with you, I can't tell you why Squid is such an issue. But I've identified that as an issue when I was attempting to get Squid with SquidGuard up and running myself. I've switched to E2 Guardian and have never looked back. It generates the certs without issues and works a lot better in general.

                    D 1 Reply Last reply Reply Quote 0
                    • D
                      denisk @pfsensation
                      last edited by

                      @pfsensation thanks for your response.
                      I tried e2guardian, but in it actual version appears some trouble: i need, that ALL HTTP/HTTPS traffic follows via ICAP server on another machine. In Squid, it was like:
                      icap_enable on
                      icap_send_client_ip on
                      icap_send_client_username on
                      icap_service service_req reqmod_precache bypass=0 icap://192.168.88.16:1344/echo
                      adaptation_access service_req allow all
                      icap_service service_resp respmod_precache bypass=0 icap://192.168.88.16:1344/echo
                      adaptation_access service_resp allow all

                      e2guardian sends to ICAP server only requests with some content.
                      For me, connection with ICAP is main purpose of proxy working!

                      P 1 Reply Last reply Reply Quote 0
                      • P
                        pfsensation @denisk
                        last edited by

                        @denisk Hmm... I haven't attempted that particular configuration. I use E2 Guardian for content filtering, but since it allows group setup I've got different configurations in place. For my use case it's perfect because it does generate those fake certs correctly and does a decent job of filtering.

                        For the LAN and Wi-Fi, I do full MITM and then on guest WiFi I use a equivalent to Splice all. This allows me to have CA certificates deployed onto the machines I manage. And then filter guest devices without any CA.

                        D 1 Reply Last reply Reply Quote 0
                        • D
                          denisk @pfsensation
                          last edited by

                          @pfsensation ok, i understand you. But i need to process any HTTP/HTTPS requests of all, users, which traffic follows through pfSense, except public WiFi, on another machine.
                          Squid's support responded me, that Squid-3.5 is no longer supported.
                          New question to pfSense developers - why users can updated squid to new version?

                          P 1 Reply Last reply Reply Quote 0
                          • P
                            pfsensation @denisk
                            last edited by

                            @denisk I've been waiting for the updates version on pfSense too. Squid 3.5 in my usage slowed down the Internet rather than helping it speed up through caching.

                            1 Reply Last reply Reply Quote 0
                            • T
                              thanhonap Banned
                              last edited by

                              This post is deleted!
                              1 Reply Last reply Reply Quote 0
                              • First post
                                Last post
                              Copyright 2025 Rubicon Communications LLC (Netgate). All rights reserved.