Need Help: Routing Entire Traffic Through VPNs Based on Specific Sites

VPN
1

I’m setting up a Proxmox server at home where I route my own VPNs (Oracle Always Free) as well as access Kaspersky VPN and ClearVPN. My goal is to ensure that when someone on my network attempts to access a specific site (like Twitter), the traffic is automatically routed through a particular VPN to bypass any government blocks or censorship.

As a Brazilian, I’m particularly concerned because a recent political court decision—similar to those in Venezuela—resulted in Twitter being blocked. This is why I’m looking for a solution.

My question is: is there any software that can detect when specific sites are being accessed on the network and automatically route that traffic through a designated VPN? For example, if someone tries to access Twitter, can it automatically route that connection through ClearVPN, Kaspersky VPN, or my existing OpenVPN?

I’ve heard about pfSense as a potential solution, but I’ve also seen comments suggesting it might not work well with Proxmox. Can anyone confirm this or suggest alternatives?

Thanks for any help!

2

The term you’re probably looking for is split-tunneling, a lot of VPN options out there that can handle it.

3

The easiest thing to do is route all traffic through the vpn. Or you got two choices TLS SNI based routing and DNS based routing. You could do ip don’t recommend it. Pfsense could possibly do this all though have never set it up but the only two things that are clear are DNS queries and TLS cert names. DNS is going to much easier but again the easiest way to do all this is just send all your traffic through the VPN. Because management of all the domains of what does and doesn’t go through it will be a huge time soak and hassle. I recommend setting up two vpn tunnels to two different providers with failover to one.