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    ONE Windows Server 2012 box cannot ping through S2S VPN

    Scheduled Pinned Locked Moved OpenVPN
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    • H
      Helix26404
      last edited by

      I will preface by saying I am about to rip my hair out over this issue. The answer is probably right in front of me, but I have been spinning around for half a day trying to figure this out and have the problem isolated but can't figure it out.  >:(

      Background: I am migrating from a Rackspace cloud environment to an Azure cloud environment. I have a pfSense network appliance provisioned in Azure and a Vyatta vRouter network appliance provisioned in Rackspace. I have created a OpenVPN tunnel between those two appliances to facilitate the migration.

      Rackspace subnet - 172.20.10.32/27
      Azure subnet - 10.0.0.0/24
      OpenVPN tunnel - 192.168.100.80

      Every VM in the Rackspace subnet can ping each other and the Vyatta appliance. Every VM in the Azure subnet can ping each other and the pfSense appliance.

      Every VM in the Azure subnet can ping every VM in the Rackspace subnet over the VPN tunnel EXCEPT a single Windows Server 2012 VM. That Windows VM also can't ping any VM in the Azure subnet NOR can it ping the VPN tunnel interface (192.168.100.80). That Windows VM CAN be pinged by the Vyatta, which has the VPN interface enabled on it.

      All of these facts leads me to believe there is something acting at the application layer on the Windows device (firewall, A/V, etc.) blocking these ping responses for whatever reason. I have disabled Windows Firewall, etc. My other thought was the route to the pfSense appliance wasn't being advertised to the Windows box by the Vyatta appliance, but if that were the case, the Linux VMs would also have the same problem.

      Again, it's that one Windows box. What am I missing here? Obvious answers are welcome, as I feel I am missing something right in front of me…

      Thanks!

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      • V
        viragomann
        last edited by

        Is there a different default gateway set on this Windows server, another than the Vyatta?

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