Just tested this...
On iOS8, if using VPN on Demand configured for a private TLD (like ".int" or ".mine"), using Safari to browse to "mysite.int" or "mysite.mine" no longer activates VPN on Demand.
You'll need to visit the domain ".int" or ".mine" directly in a browser to activate the VPN and make "mysite.int" or "mysite.mine" function properly.
Hope this helps someone,
Dominic
iOS8 VPN on Demand bare-TLD profile bug (and fix!)
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