IPSEC + Commercial SSL
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We setup and tested the IPSEC + self signed cert and it worked 100% on Mac's and Windows 10.
Then we went to deploy...
I've run into two different types of Mac users in the field. The first ones generally can't follow directions (they just aren't techie enough and it's hard to guide them through over the phone) and the second ones, well they are the ones that won't do anything that requires you to enter a password on their system (worried you are trying to do something malicious).
The challenge is we don't have physical access to these boxes as they are fully remote.
So the decision was made to just get a public SSL. This worked great with the Mac users but then suddenly the Windows 10 users could no longer connect, even though the only change was the commercial SSL.
Is there something about a commercial SSL that needs to be handled differently with IPSEC to make it work with Windows 10?