IPsec from Azure pfSense VPN appliance to on-premises box

  • I successfully started an IPsec VPN tunnel from my Azure pfSense VPN appliance to an on-premises box.  But I cannot flow traffic from my Windows Server VM in Azure through that IPsec.

    IOW, I can ping my on-premises box at internal LAN IP from the pfSense appliance at Azure virtual network IP  I can ping the pfSense appliance at from the Windows VM at  But I cannot ping my on-premises box at from the Windows VM at

    Azure's virtual network's address space The Windows VM is on Azure subnet  The pfSense VPN appliance is on Azure subnet

    I have a route set up to next hop if the destination is  That route is associated with subnet

    I believe I have the right firewall rules in the pfSense appliance.

    I should add there is also an Azure VPN Gateway on Gateway Subnet, which I have used to successfully ping from 192.1680.4.  What I am trying to do is replicate that success with the pfsense Virtual VPN device.  I would have thought the route I set up would have redirected traffic to the pfSense.  But so far something is not working.

    Any suggestions would be very helpful.

    Thank you!


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