VPN chaining not working – Rubin Shrestha

Motivation

I’m trying to use a VPN tunnel to convince my company’s servers that I am in country A, even though I’m in country B. Last time I was in country B, this was not working, and I was unable to access outlook, teams, etc. Bad times. Now I’m back and trying to improve my setup before I head over to country B again.

My understanding

I’m working off the following premises:

If I create a VPN connection, from my work laptop, to a VPN server in country A, I should appear to be in country A and there is no way of knowing, I’m physically elsewhere.
This holds, even if I then create another VPN connection from the same laptop, e.g., to the company’s VPN server. (This part is irrelevant for the current question.)

If these are incorrect, or only partially correct, I’d appreciate a correction.

Testing setup

Currently, I need help with my testing setup.

Because I’m currently in country A, I’ve created a VPN connection (via ExpressVPN) to country B. whatsmyipaddress shows me as being in country B. And I can indeed not access outlook and teams:

So far, so good; this is all as expected.

Now, to test things, I want to connect to my wireguard VPN server back in country A. So, when exiting the tunnel in country B, the second tunnel should make it appear again as if I’m in country A. (So that I can then investigate, if that is actually true and if so, why I cannot access the services.) (I believe this is called “VPN chaining”, and I have seen some related questions, like here and here, but I’m too much of a noob to understand them.)

Issue

However, this is not working. As soon as I connect the second tunnel (using the wireguard client on the same laptop as where the ExpressVPN client is), I have no internet access anymore.

Is there an obvious reason why this could not work the way I’m invisioning it? Is there a VPN setting I need to change here? (IPSec vs TTL?) Is there a different/better/working solution to get my testing setup working?