IIRC from when I looked at this, I was able to have two completely different 
servers configured on my Win10 client, and it worked correctly. I think the 
trick is to make sure that each VPN server has a different hostname (duh), and 
that the VPN SAN keys in the certs contain the FQDN hostname.



From: Tobias Brunner<mailto:[email protected]>
Sent: Monday, February 25, 2019 3:30 AM
To: Tom Rymes<mailto:[email protected]>; 
[email protected]<mailto:[email protected]>
Subject: Re: [strongSwan] Windows Client - Multiple Connections, Multiple Certs



Hi Tom,

> I do not see anywhere that I
> can specify which certificate the client should use for a given connection.

I think you can only do that with EAP-TLS (i.e. not with machine
certificates) where you might actually get prompted for a certificate if
there are multiple and the advanced VPN options (via adapter options on
Windows 10) even provide a setting to pre-select a specific certificate
to use (via issuer/CA and/or EKU).

Regards,
Tobias


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