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I'm trying to setup a Point-to-Site VPN using Azure VNet Gateway that would expose the LAN behind the client.

I've done this with success using OpenVPN (using route and iroute) but I couldn't find any documentation that supports that this would work on Azure.

My idea is to connect an On-Premises machine to the VNet, creating an Hybrid Network, that VNet would have routing rules that would route the traffic to my On-Premises LAN to the VPN Client.

That VPN Client would have packet forward enabled, pushing the packets to the correct destination on LAN.

Has anyone done anything similar on Azure? A diagram would be:

LAN <--> On-Premises Server connected to VNET through VPN <--> Azure VNet

Best regards Tiago

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Are you using Point-to-Site VPN because of the lack of an VPN capable Firewall/Router?

If that is the case, you could also use the RRAS server role in Windows Server 2012/2016 to achieve the same. This should be more stable that the using the point-to-site VPN to route your clients to Azure, and may avoid some routing limitations.

Here are some good resources to get you started:

https://blogs.technet.microsoft.com/jletsch/2016/03/15/lets-configure-azure-site-to-site-vpn-with-rras-in-azure-resource-manager/

https://scomandothergeekystuff.com/2016/09/19/creating-a-site-to-site-vpn-with-azure-resource-manager-arm-and-windows-2012r2/

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