So, at the main site, when the tunnel is down, the Shoretel switch will realize this and use the PSTN failover number, assuming you have it configured correctly for the user at the remote site.
I would watch the trunk test tool and see what happens when you try to use PSTN Failover.
This is also assuming that the user is at this remote site with a PSTN trunk.
Theres not much configuring that needs to be done and it sounds like you have it configured correctly. Watch in the trunk test tool to see if it does attempt to dial out, then make sure its dialing the right number. If it is, it should be hitting your switch at the remote site and then on to the user...
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