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As things stand today, I have a site-to-site VPN between on-prem and Azure which works well.

I am currently using an SSL VPN to my on-prem, but would like to migrate my clients to all use Point-to-Site VPN in Azure since we're moving all of our key infrastructure there. In my perfect future case, Azure is the core of everything, and my local on-prem is just a glorified hotspot where my users don't have to VPN from and it's faster.

I can ping back and forth from Azure to On-Prem, and my SSL VPN clients can ping into either Azure or On-Prem subnets with no problem. However, when my clients connect to Point-to-Site in Azure, they can ping VMs running in Azure, but they can't reach any systems on my local On-Prem network. This will cause challenges for the migration because it means I basically have to "big-bang" the cutover rather than moving things as it makes sense.

Here's the setup:

Local Site - 10.0.20.0/24  < ---- Site to Site VPN ----> Azure Site - 10.0.40.0/24
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Local VPN Client - 10.0.30.0/24                   Azure Point-to-Site VPN - 10.0.50.0/24

Basically, trying to understand what I might be missing that would prevent clients on Point-to-Site from getting back to the local Site. I've checked firewall rules on the local site side, but the packets don't ever seem to even be showing up there in a packet dump.

Of interest, my best guess at this point after troubleshooting is that the IKEv2 Proposals list 10.0.20.0 <-> 10.0.40.0 and 10.0.30.0 <-> 10.0.40.0, but there's no way to get a tunnel for 10.0.20.0 <-> 10.0.50.0 to come up since Azure auto brings it up based on the subnet configuration and I can't seem to make the Point-To-Site subnet part of a subnet I've defined as part of the VNet connection. I'm wondering if that means Azure wont route from the P2S subnet back to the local site since it doesn't match a Phase 2 proposal, and if so, is there any way to make the Azure side add it so I can bring that up as part of the tunnel.

Any help is appreciated

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I've tested your plan in my lab and it works for me.

If your site-to-site VPN and point-to-site VPN both work properly, then the most possible cause of this issue would be the missing routing entry for Azure VPN client.

Please make sure that the local VPN device has the correct routing entry for Azure client and it should be routed to the Azure.

I tested your plan with RRAS, and the 10.50.1.0/24 is the subnet of my Azure VPN client.

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