I set up a point to site VPN from my computer to my vnet in Azure. Everything connects normally and even on the portal it says the tunnel is established.

When connected to the VPN, I am still unable to RDP to my server using its local IP. I verified the proper routes are in place using the route print command.

Am I missing an endpoint or something?


Affinity Groups are no longer a thing. Regions are the grouping mechanism now.

Make sure your VMs and VNet are in the same Azure Region (such as East US 2, in my case).

I can successfully connect to my VPN (Point-to-Site) and RDP to my IaaS VMs, without any Endpoints exposed.


Nothing wrong with the way you have configured your Azure Point-to-site VPN.This is a known issue ( to Microsoft, not by us!). I just blogged about it today. In a nutshell:

“IMPORTANT NOTE regarding existing virtual machines: As of the current release you must create new VMs and attach to the VPN affinity group during the Azure VM setup process”



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