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    Verifying SSL site certificate verification

    Scheduled Pinned Locked Moved General pfSense Questions
    21 Posts 7 Posters 3.5k Views
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    • DerelictD Offline
      Derelict LAYER 8 Netgate
      last edited by

      With SSL MITM you can't. If you want to verify certificates (and who doesn't?), don't do that.

      Chattanooga, Tennessee, USA
      A comprehensive network diagram is worth 10,000 words and 15 conference calls.
      DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
      Do Not Chat For Help! NO_WAN_EGRESS(TM)

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      • J Offline
        Jdwind
        last edited by

        But SSL MITM is more security (in my opinion, if I'm not wrong?), how to otherwise filtering https sites with proxy?

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        • DerelictD Offline
          Derelict LAYER 8 Netgate
          last edited by

          Well, then you have a choice to make.

          Look at https peek/splice

          Chattanooga, Tennessee, USA
          A comprehensive network diagram is worth 10,000 words and 15 conference calls.
          DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
          Do Not Chat For Help! NO_WAN_EGRESS(TM)

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          • johnpozJ Online
            johnpoz LAYER 8 Global Moderator
            last edited by

            More security for who exactly? You can filter users from going to sites you don't want them to go to without having to do a MITM on the ssl.  If your doing a MITM the user would not be able to see the end cert, only the cert you present them.

            An intelligent man is sometimes forced to be drunk to spend time with his fools
            If you get confused: Listen to the Music Play
            Please don't Chat/PM me for help, unless mod related
            SG-4860 24.11 | Lab VMs 2.8, 24.11

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            • J Offline
              Jdwind
              last edited by

              Thank you very much for a explnation, but can you tell me how can I filter sites with SSL and the same time have anti-virus protection enabled for them?

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              • johnpozJ Online
                johnpoz LAYER 8 Global Moderator
                last edited by

                You would not be able to scan for antivirus inside a ssl tunnel.  The client would do this on their end..  You wouldn't do this on the firewall.

                But you can filter what sites they go to without having to do a mitm on the ssl.. Doing mitm opens up a whole can of worms.. You would then be able to sniff users passwords to like their banks, and such.  View medical info they might be looking at.

                SSL is suppose to provide end to end security.. From the end user to the site they are going to.. When you break that trust by doing a mitm you can open up a whole freaking can of issues that are best left alone..

                An intelligent man is sometimes forced to be drunk to spend time with his fools
                If you get confused: Listen to the Music Play
                Please don't Chat/PM me for help, unless mod related
                SG-4860 24.11 | Lab VMs 2.8, 24.11

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                • J Offline
                  Jdwind
                  last edited by

                  So, if you can (please), tell me, what should I do to do? Use transparent squid proxy without MITM? And how to manage ssl sites (i.e. how to block youtube, facebook etc. for some users in my network)?
                  Best regards and thank you very much.

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                  • DerelictD Offline
                    Derelict LAYER 8 Netgate
                    last edited by

                    peek/splice, not MITM.

                    Chattanooga, Tennessee, USA
                    A comprehensive network diagram is worth 10,000 words and 15 conference calls.
                    DO NOT set a source address/port in a port forward or firewall rule unless you KNOW you need it!
                    Do Not Chat For Help! NO_WAN_EGRESS(TM)

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                    • J Offline
                      Jdwind
                      last edited by

                      Then what should I to do? Disable MITM, enable transparent proxy in squid? I found only in Squid (in SSL Man In the Middle Filtering section) that information: Please see SslBump Peek and Splice wiki documentation for additional details - but there http://wiki.squid-cache.org/Features/SslPeekAndSplice is not information how use it with Pfsense. Can you tell me some more about how do that, please?

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                      • C Offline
                        Chrismallia
                        last edited by

                        Here is mine

                        sp.PNG
                        sp.PNG_thumb

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                        • D Offline
                          doktornotor Banned
                          last edited by

                          @Jdwind:

                          But SSL MITM is more security

                          https://www.us-cert.gov/ncas/alerts/TA17-075A

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                          • J Offline
                            Jdwind
                            last edited by

                            Thank you, doktornotor. I have installed end-point antyvirus on every host too. In my network I must have any security solution (like IPS/IDS - I use Snort package), that why I used MITM and SSL filtering. Chrismallia show his configuration, but if I am not wrong he has MITM and SSL filtering too. Only different is with SSL/MITM mode - I have default, he Splice All. That's all?

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                            • C Offline
                              Chrismallia
                              last edited by

                              with splice all you do not need to install certs on devices, it is mostly good for only filtering  no AV, so it does not break the  ssl connection  or inspect content, it uses the SNI, anyone correct me if I am mistaken in any way

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                              • D Offline
                                doktornotor Banned
                                last edited by

                                @Jdwind:

                                Thank you, doktornotor. I have installed end-point antyvirus on every host too.

                                Oh noes. That was NOT the point. The point was that MITM is evil.

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                                • J Offline
                                  Jdwind
                                  last edited by

                                  I tried this settings (from Chrismallia) on virtual network, Pfsense and two hosts and  what can I say… it works. Antivirus dont works with SSL, but I have it installed on every host. Thank you all for help and explanation very, very much. But one thing more that I can't understand (after Doktornotor post) - it is still MITM enabled - does it matter?
                                  Best regards

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                                  • johnpozJ Online
                                    johnpoz LAYER 8 Global Moderator
                                    last edited by

                                    no with splice your not your doing a peek and then splicing it back.. The client is getting the actual cert from the server.. Your just peaking inside to see where they are going, etc.  And if it should be filtered.

                                    "splice: Become a TCP tunnel without decoding the connection. The client and the server exchange data as if there is no proxy in between."

                                    An intelligent man is sometimes forced to be drunk to spend time with his fools
                                    If you get confused: Listen to the Music Play
                                    Please don't Chat/PM me for help, unless mod related
                                    SG-4860 24.11 | Lab VMs 2.8, 24.11

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                                    • J Offline
                                      Jdwind
                                      last edited by

                                      Thank you very much again, so now I have everything ok. With Squidguard ssl filtering just works.

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                                      • H Offline
                                        Harvy66
                                        last edited by

                                        There are many attack vectors to infect machines when MITM is used. SSL provides two things, privacy and security. The security is provided by the signing. When you MITM, you break the signing, which means you break the security.

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                                        • K Offline
                                          kpa
                                          last edited by

                                          With MITM you're breaking the chain of trust normally provided the trusted third party signatures found on the certificates. Your users will no longer be able to verify that they are connecting to the real deal when they connect to a HTTPS site, instead they can at maximum be sure only that they are connecting to your MITM proxy.

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                                          • J Offline
                                            Jdwind
                                            last edited by

                                            It is too much  for my mind… Yes, now I know you are both right. But now, when I'm using peek and splice all mode with MITM and I can see every certificate verificated by.. i.e. Verisign, Symante, Oracle.. now my network settings are right - am I right or am I wrong?
                                            EDIT:
                                            I found that thread https://forum.pfsense.org/index.php?topic=123461.0, there is more explanation about my doubts. Thank you once more.

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