Can you ping the remote computer and get a response back? If you can, that means the tunnel is established. From your description that sounds like it is happening; however, I suspect your problem might be related to the MTU.
Look at the VPN Setup Guide (
http://www.wingate.com/files/VPN_Setup_Guide.pdf) for more information on testing for MTU problems and how to resolve it.
I've pasted the basic text in below, but there are many more diagnostic you can run. If this does turn out to be the case, there are several tools you can use to adjust the MTU - if you're using version 6.0 of WinGate or 2.0 of WinGate VPN you can adjust it in GateKeeper. Alternatively,
http://www.dslreports.com/drtcp, has a tool that will do it too.
VPN Setup Guide wrote:On some types of connection, there is a reduction in the MTU (Maximum Transmission Unit, which is a measure of the largest packet payload that may be sent over a network interface or point to point link). For instance PPPoE connections reduce the MTU by 8 bytes. The standard MTU for Ethernet is 1500 bytes, which means you can have up to 1500 bytes of payload over Ethernet. The Ethernet frame itself has a 14-byte header, so the actual maximum packet size (as opposed to the MTU) is 1514. WinGate VPN reduces the MTU as well, since the encryption and tunnelling require approx 50 - 60 bytes per packet.
If there are MTU issues, you can find that large (maximum size) packets can be lost. This produces strange effects such as:
Able to connect to a network share, prompted for a password, etc. but unable to browse large directories or transfer files.
Network drive mappings are disconnected and are generally unreliable.
Using Ping, you can send packets of different sizes. WinGate VPN fragments packets (if allowed) when it transfers them across the VPN. Therefore you should be able to send large ping packets successfully across the VPN if everything is working properly. If not, then once you get to a certain size, they will stop working.
To send a packet of a certain size, use the -l switch on the ping command. e.g.
ping 192.168.1.1 -l 1422
This will send a ping packet with a 1422 byte ICMP payload. It is important to note that the actual packet size of the ping packet is 28 bytes larger than this since the IP plus ICMP headers use 26 bytes. Therefore the example above will send a packet of 1450 bytes (not including the Ethernet header). The Ethernet header is not counted because this is stripped off and not transmitted over the VPN.
By working out the ping size that works vs the size that doesn't you can calculate what the effective MTU really is. For dialup connections and some network interfaces, it is then possible to modify the MTU so that your client machines will no longer send packets that are too big.