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To give some idea of the network architecture and the issue;

Head Office has a Pfsense firewall with a site-to-site IPSec VPN connection to some virtual machines in Azure. When on site (192.168.1.1/22) I have no issues communicating to the Azure VNET (10.0.0.0/16) or its VM's.

Remote users connect to head office using OpenVPN on Pfsense (10.8.0.0/24)and can access site resources but can't see the Azure VNET.

I tried adding the route to the OpenVPN server config (push "route 10.0.0.0 255.255.0.0"), but that made no difference.

Any direction on how to make the AZ VNET visible to remote users would be appreciated.

thenickmarks
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  • 10.8.0.0/24 is inside 10.0.0.0/16 so when a packet comes from say 10.8.0.2 > 10.0.0.2 then 10.0.0.2 might think that 10.8.0.2 is on the local net and never go back the IPSec route. Try to write a map of how the traffic should flow, and then consider which routes you need for each packet to reach the destination in each device/router. Remember that it needs to flow both ways. – NiKiZe Jan 19 '22 at 08:51

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