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Originally Posted by sjforcum
Sounds like the TCP isn't setup on your VPN...so the packets are getting blocked.
SJF
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If that were the case the phone would not work at all.
VPN tunnels are nothing more than encapsulated, routed traffic - the broadband equivalent of a leased line, if it makes it easier to grasp. The gateways utilize strong encryption to prevent the content of the packets from being read by standard sniffing tools, but they don't arbitrarily block or drop packets (unless they are defective).
Is the problem with a single phone or all phones? Have you tried testing the same phone from within the same LAN segment as the server?
Do you have a PC on the network where the phone is? Set up an extended ping to the IP address the phone is connecting to and watch for drops. If you don't lose packets, or other applications are running ok across the tunnel, you can pretty much rule out it being the network.