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Unable to on outlook after connecting Open VPN

Scheduled Pinned Locked Moved OpenVPN
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  • S
    shiv_znet
    last edited by shiv_znet Sep 25, 2019, 1:08 PM Sep 25, 2019, 1:04 PM

    Hello Everyone,

    Last couple of days we are facing some issues with PfSense. When we connect a user from a remote location via Open VPN then after connecting VPN everything is working fine. but we are unable to connect outlook only after connecting Open VPN and getting below error. are disconnected VPN outlook is working fine.

    RightNow we are using office365 for mailing services.

    Error - We are unable to connect right now. Please check your network and try again later
    Firewal IPS Version - 2.3.5-RELEASE (amd64)

    G 1 Reply Last reply Sep 26, 2019, 6:43 AM Reply Quote 0
    • J
      johnpoz LAYER 8 Global Moderator
      last edited by johnpoz Sep 25, 2019, 1:22 PM Sep 25, 2019, 1:17 PM

      For starters pfsense 2.3.5 has been EOL for quite some time.. Update to current if you want any sort of help.

      Oct 31 will be a YEAR since it was eol, and there was even a year before that warning that it was going to be no longer supported.. And your not even running the latest version of that p2? Why should anyone waste any time helping someone that can't even keep their firewall even somewhat current?

      Not meaning to rant at you specifically, but this is just nonsense to be running such an old version of your FIREWALL.. meant to protect your network, etc..

      Does MS support windows 98 still? ;)

      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
      • S
        shiv_znet
        last edited by Sep 26, 2019, 6:24 AM

        Hello Everyone,

        Please suggest for the same and let us know why we are getting such types of issue.

        1 Reply Last reply Reply Quote 0
        • G
          Gertjan @shiv_znet
          last edited by Gertjan Sep 26, 2019, 6:44 AM Sep 26, 2019, 6:43 AM

          @shiv_znet said in Unable to on outlook after connecting Open VPN:

          to connect outlook

          @shiv_znet said in Unable to on outlook after connecting Open VPN:

          we are using office365 for mailing services.

          Sorry, I don't know all Microsoft mail services.
          So, please detail : are you using Office 365 Outlook, the fat mail client ? A web-mail service ?
          What URLs, ports, protocols ?

          @shiv_znet said in Unable to on outlook after connecting Open VPN:

          Error - We are unable to connect right now. Please check your network and try again later

          The error states, that you can't connect to ... where ever you want to connect to.
          Your are connected as a client to pfSense using the OpenVPN server, right ?
          What are the firewall rules on the OpenVPN interface tab ?

          Btw : your pfSense didn't change lately. I guess it didn't change for the last year or two. So, if there are issues, it must be the settings.
          So, tell us, what (did you) change ?

          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
          • D
            Derelict LAYER 8 Netgate
            last edited by Sep 26, 2019, 7:37 AM

            Regarding the known issue of Microsoft Office products failing to work on Windows 10 with OpenVPN, the root cause appears to be that the Network Location Awareness (NLA) and Network Connection Status Indicator (NCSI) services will not function without a default gateway set for the OpenVPN interface.

            The workaround illustrated in this blog post appears to work as advertised.

            For additional support with this specific issue, please see https://support.microsoft.com/en-us.

            It is not possible to resolve the issue from the pfSense side and this is strictly a Microsoft issue. It will require Microsoft addressing the underlying behavior of their software before this workaround will no longer be needed.

            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
            • D
              Derelict LAYER 8 Netgate
              last edited by Sep 26, 2019, 7:38 AM

              It is not pfSense or OpenVPN. It is Windows.

              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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              • G
                Gertjan
                last edited by Sep 26, 2019, 8:20 AM

                Furthermore : the solution talks about a TAP OpenVPN solution.
                TAP : that's pretty like your asking for troubles.

                Anyway, I'm using Office 365 myself @ home.
                It happens rather often that I'm connected to work, using the OpenVPN client delivered by pfSense, connected to the OpenVPN server exposed by pfSense.
                Everything works well. Maybe I don't have any issues because : I'm using TUN and IPv6 over VPN ....

                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
                • D
                  Derelict LAYER 8 Netgate
                  last edited by Derelict Sep 26, 2019, 8:25 AM Sep 26, 2019, 8:24 AM

                  Up to Microsoft to solve. There is nothing wrong with the OpenVPN /1 "default" route solution. In fact, it's pretty simple and elegant. As I understand it, Microsoft has hard-set something to do with the 0.0.0.0/0 route on the workstation which is just dumb. This is up to them to fix. That is where any torches and pitchforks should be taken.

                  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
                  • S
                    shiv_znet
                    last edited by Sep 26, 2019, 2:19 PM

                    Hello Everyone,

                    Today we observed that when we are using updated version - 16.0.11328.20420 of Microsoft outlook then getting this error.

                    When we use the lower outlook version then all things are working.

                    Please suggest what can we do????

                    1 Reply Last reply Reply Quote 0
                    • J
                      JKnott
                      last edited by Sep 26, 2019, 3:08 PM

                      @shiv_znet said in Unable to on outlook after connecting Open VPN:

                      Please suggest what can we do????

                      Stop using Outlook! 😉

                      PfSense running on Qotom mini PC
                      i5 CPU, 4 GB memory, 32 GB SSD & 4 Intel Gb Ethernet ports.
                      UniFi AC-Lite access point

                      I haven't lost my mind. It's around here...somewhere...

                      1 Reply Last reply Reply Quote 0
                      • G
                        Gertjan
                        last edited by Sep 27, 2019, 6:14 AM

                        ... or take the OpenVPN using the horrible TAP out of the equitation.

                        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
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