Celeb Glow
general | March 01, 2026

Simple way to Daisy Chain multiple VPN connections in Windows?

We have a VPN which lets us access a wide area network which we need in to in order to get access to some servers. However, we're not allowed to access the servers from the IP that the VPN tunnels to. We need to remote onto a different server, and from there we access the servers we need on to.

When we connect to the VPN, we lose all internet access, so I had the bright idea of setting up the VPN stuff inside of a virtual machine. This would be fine if we could access the servers from the first VPN, but that's a right pain. The server we remote on to only has 2 connections allowed onto it. I'm wondering if there's a way to connect onto a VPN, and from there, have another VPN be running which tunnels our connection to the server which is allowed to access the servers we need on to from.

Having the VPN installed on the host machine is not an option. Nesting virtual machines is not an option.

Thanks

3 Reset to default

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