1) When trying to connect to work it says "contacting the security gateway x.x.x.x" and never prompts me for my username and password.
kdalf,
It is possible and very common that some organizations do not allow ipsec vpn ports or it Ipsec is allowed on a per user basis,this is just one possibility. Another possibility may be they do not allow IPsec vpn on their wireless vlans, either or what you may need to do is to contact the net administrators and ask them to ensure that IPsec vpn ports are indeed allow or not, my guess it is not. If asking is out of your reach you could also ask if anyone else in the same area you are connecting from have successfully connected to their work via IPsec.
2) Going to the coffee shop down the street, it works fine on their wireless. So I know its not a setting on my computer (trust me, its not a firewall setting for a specific network zone ither).
This explains my answer in question 1, the coffee shop does allow ipsec vpn ports, this is nice to attract more custumers :)
3) When I tried to VPN from the "broken" network, and didn't have "Enabled Transparent Tunneling" enabled, it DOES prompt me for my username and password and it shows its connected with the lock in the bottom of the start menu. However I can't ping or do anything on that remote network.
This one prety much relies on the issue in question 1.
4) THe TCP tunnel to port 10,000 is blocked with my work.
Ipsec over TCP port 10,000 is usually implemented at the RA vpn server, so if you choose in your client IPsec over tcp on port 10,000 you must be aware that the RA VPN server must also be configured to support it
5) IP SEC over UDP doesn't work ither
6) I'm at a school network and i think they have blocked something, I don't know but i'm guessing its UDP ...
Q 5 & 6 Same answer as question 1,
The workaround is much based on whether your school does allow ipsec ports, you need to conatct the network administrator before trying to troubleshoot vpn client software.
Rgds
Jorge
Jorge Rodriguez
