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VPN Connection on Azure VM


I have an Azure VM which I connect to via RDP. From there I need to use Check Point Endpoint Security to connect to a third party network in order to collect some data. 

However, once I connect the VPN, my RDP connection gets disconnected and as it detects I've disconnected it also kills the VPN connection.

What do I need to configure in order for my VPN connection not to disconnect my RDP session? I've tried setting the default gateway on the virtual adapter to the same one my VM uses but that makes no difference. Firewall rules are set to allow Checkpoint through... admittedly my network skills aren't the best but I can't help feeling there is something simple I'm not doing here, would anybody be able to advise?

Many thanks,


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2 Replies

Sounds like the VPN might be rerouting the connection thru itself.

Are you connecting to the VM via RDP directly thru the Internet?

Any Security Gateway in Azure that could potentially NAT the RDP connection?

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Hello, did you managed to resolve this issue? I am facing same problem 😉

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