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

    Certificate Error when accessing email on optional Interface

    Scheduled Pinned Locked Moved General pfSense Questions
    7 Posts 5 Posters 1.9k 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.
    • F Offline
      fredfred5
      last edited by

      Hi Guys,

      I have a strange problem with a firewall I have deployed.

      It has 1 WAN and 3 LANs

      LANs are as Follows:

      LAN - 10.0.0.0/16
      DMZ - 192.168.1.0/24 (OPT1)
      WIFI - 172.16.0.1/16 (OPT2)

      When users are connected to the LAN, they have no issues and can get to internet and email fine.

      When connected to the Wifi interface they are able to browse the internet but cannot get to their email (Exchange 2010 on site), in the case of iphones it will not provide an error and does not download any new email. With the laptops/PCs using outlook they are getting a certificate error.

      Strangely the certificate lists the correct autodiscover domain but reports that it is issued by pfsense, it matches the webconfigurator SSL cert.

      I have checked the rules on the wifi interface and they seem correct to me.

      (Please ignore the 2nd allowed rule, that was due to some faulty thinking, I realise it is using autodiscover not internal IPs.)

      Is there some kind of SSL redirect or capture that happens for optional interfaces? Any help would be appreciated, I'm left scratching my head.

      If you guys need more info or if I have left something out please let me know.

      Thanks!

      1 Reply Last reply Reply Quote 0
      • D Offline
        doktornotor Banned
        last edited by

        Your DNS records are broken, plain and simple. NAT reflection will never work around SRV records. Point LAN clients to where Exchange is running and NOT to your WAN. (You could also move your pfSense webGUI out of 443, that won't make your DNS any less broken though.)

        1 Reply Last reply Reply Quote 0
        • johnpozJ Offline
          johnpoz LAYER 8 Global Moderator
          last edited by

          /16 on your WAN??  How does that make sense.. Same goes for your 172.16 with /16

          Do you have that many machines on the same network?

          Client internally should not nat reflect to get to your servers.. This is a HACK at best.. As dok already stated fix your dns to point to the local rfc1918 space your servers are on for machines that are also on this rfc1918 networks..

          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

          1 Reply Last reply Reply Quote 0
          • F Offline
            fredfred5
            last edited by

            @doktornotor:

            Your DNS records are broken, plain and simple. NAT reflection will never work around SRV records. Point LAN clients to where Exchange is running and NOT to your WAN. (You could also move your pfSense webGUI out of 443, that won't make your DNS any less broken though.)

            Of course! that makes much more sense, I'll set my DNS record to direct to the LAN IP of exchange.

            Thanks

            1 Reply Last reply Reply Quote 0
            • GertjanG Offline
              Gertjan
              last edited by

              @fredfred5:

              I have checked the rules on the wifi interface and they seem correct to me.

              Besides rule 2, you can also ignore rule 3 and 4 right now.
              Rule "1" will be valid for ALL TCP connection - rule 2 is just a subset of 1.
              If you want to have rule 3 and 4 working for you, put them on position 1 and 2.

              No "help me" PM's please. Use the forum, the community will thank you.
              Edit : and where are the logs ??

              1 Reply Last reply Reply Quote 0
              • DerelictD Offline
                Derelict LAYER 8 Netgate
                last edited by

                Yes. ^

                Rule #2 should probably be moved to the top.  Rules 3 and 4 should probably be below that.  And what you have as rule #1 should probably be last. And protocol TCP should probably be changed to protocol any in #3 and #4.

                The general scheme for guest networks is:

                Pass specifically the local assets you want guests to be able to access (DNS, Exchange, Email, etc)
                Block less-specifically the local assets you don't want them to access (LAN net, This firewall, etc)
                Pass everything else (The internet)

                https://doc.pfsense.org/index.php/Firewall_Rule_Basics

                https://doc.pfsense.org/index.php/Firewall_Rule_Processing_Order

                https://doc.pfsense.org/index.php/Firewall_Rule_Troubleshooting

                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)

                1 Reply Last reply Reply Quote 0
                • johnpozJ Offline
                  johnpoz LAYER 8 Global Moderator
                  last edited by

                  Rule 2 should be moved to the bin.. What point is it if you already allow wifi net to go anywhere..  Is that address on a different segment than wifi net?  If on same as wifi net also pointless.

                  As to 3 and 4 they could be removed by making 1st rule a ! alias that includes your other networks.

                  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

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