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IPsec site2site tunnel connected but not able to telnet/ping the other end


I've followed the microsoft guide on setting up an IPsec site2site tunnel here.

Setting this up has been successful and I'm able to see it successfully connected. To create some traffic and further test the connection I set up a VM, connected to its public IP, and tried to ping / telnet and Test-Connection on Powershell. But none of these were able to create some traffic.

I haven't been able to find any tutorials/guides etc. that actually go into the VM to test the connection. In the Microsoft guide it seemed to say something about the VMs private IP, but I'm not able to connect using the private IP, not sure why. This might be the issue. My VM is a windows datacenter 2019. Sorry for the open-ended question but I don't know where to go from here.

What might be reasons I can't ping the IPsec tunnel?


Solution

  • It looks like you have verified the VPN connection and its status is 'Succeeded' and 'Connected'.

    The best way to initially verify that you can connect to your VM is to connect by using its private IP address.

    You can find the Azure VM's private IP address from the Azure portal, and RDP connection to that Azure VM with its private IP address. If you can't RDP to that VM, see https://learn.microsoft.com/en-us/azure/vpn-gateway/vpn-gateway-howto-site-to-site-resource-manager-portal#to-troubleshoot-an-rdp-connection-to-a-vm

    Also, for network connection test, you should avoid associating a network security group (NSG) to that gateway subnet. Ensure there is no firewall blocking the RDP connection between the local machine and azure VM. Such as NSG or firewall inside the Azure VM and the local machine.

    For more information:

    Troubleshooting: Azure Site-to-Site VPN disconnects intermittently

    Troubleshooting: An Azure site-to-site VPN connection cannot connect and stops working