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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

      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)

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

        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

          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
          • GertjanG
            Gertjan @shiv_znet
            last edited by Gertjan

            @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
            • DerelictD
              Derelict LAYER 8 Netgate
              last edited by

              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
              • DerelictD
                Derelict LAYER 8 Netgate
                last edited by

                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)

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

                  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
                  • DerelictD
                    Derelict LAYER 8 Netgate
                    last edited by Derelict

                    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

                      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
                      • JKnottJ
                        JKnott
                        last edited by

                        @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
                        • GertjanG
                          Gertjan
                          last edited by

                          ... 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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