Trying to run a pair of VPN connections on a macbook pro on my work device

Hello,

I work in a Mac environment locally, and on Linux/Windows VMs remotely. We have several cloud providers, the two most commonly connected to are Rackspace and AWS.

Our Rackspace VPN connects via Cisco Client connect software, and AWS via an home grown OpenVPN connection.

When running an Ansible playbook intended to connect to the entire fleet, half the connections fail, and you have to disconnect from one to connect to the other.

I didn't set any of this up, but the guy who did says he has a workaround that he seems hesitant to talk about (he's working on a Linux device and is technically breaking workplace rules).

He says he's able to connect to both via debian's network connector and VPNC. I've seen him successfully run ansible playbooks to completion with no errors so it does work.

Is there a way to do somethign similar on a Mac that I'm not thinking of?