Multiple VPN connection on Mac OS

There is a lot to this, and there may not be a simple answer.

VPNs typically work in one of two ways - either 'all-in' (all traffic is routed over the VPN connection), or 'split-tunnel' where selective traffic is routed over the VPN and other traffic uses the normal unencrypted path.

The split model is commonly based on destination IP addresses, but can be more fine-grained, but typically amends the system's routing table to say that traffic for 'x.x.x.x' should go over the VPN connection.

On that basis, it may be possible to have multiple VPN connections up that sends different traffic via a different path (e.g. 'x.x.x.x -> VPN1; y.y.y.y -> VPN2).

The specifics of this, though, will depend a lot on the VPN connection configurations and how they interact with each other. It may also be affected by the order of establishing the VPN connections.

So, the short answer to your question is 'maybe', but there are too many gotchas to be able to give a single, solid answer.

ivlvn wrote:

Hello.

Can you please tell me if it is possible to organize a double VPN connection on the mac OS? In the country where I am, many VPN protocols are blocked, and I need to work server is exactly working on such (my local VPN). I am using combination of VPN (with non-blocked protocol) on mac and VPN connection in virtual machine (tunnel in tunnel). But very often I need to connect to the work PC through the mac OS applications, which I can not do. To configure a VPN on the router is impossible, there is no access to it, I clarify at once. There is only a laptop with mac OS.

See if there is anything here—

Change VPN settings on Mac - Apple Support