Iphone

I'm having a bit of a problem with outlook 2003 trying to connect to the exchange server 2003 using SonicWall VPN Routers.

Two sonicwall vpn's Pro 2040 and TZ170 both using enhance software, site to site VPN works like a charm, can ping any computer back and forth from site to site. I can VNC if i need to, but when trying send and receive from outlook the program tries to connect but fails, i don't get an error it just says disconnected at the bottom right corner.

Contacted SonicWall support to see if it was a router issue with traffic being blocked, but they advice me that if the vpn tunnel was working correctly there is no need to create a policy to allow traffic from the vpn to the lan or viceversa, and that the whole idea of having the site to site vpn is to allow the traffic between the two location go thru, which makes sense to me.

Ran a couple test from the remote site telnet into the mail server to see if it is listenning on port 25 and i got this reply banner

220 mail_server_name.domain_name.com Microsoft ESMTP MAIL Service, Version: 5.0.2195
.6713 ready at Tue, 9 Jan 2007 19:22:12 -0500

Downloaded Ethereal to capture packets going back and forth but i did not see any packets going to or from the workstation and the mail server

And to complete the mistery if i enable the vpn software client outlook works as it used to before creating the hardware site to site VPN.

There are two computers behind the TZ170 they both have static ip's, there are no servers on this location and the router has the dhcp enable

I can't think of anything else maybe is a dns or gateway issue.

Thanks for you help guys and let me know if i missed to mention anything

Iphone

In your outlook client, are you configured using the IP or host name.

Make sure you have resolution on the host name and that it is resolving to the correct IP.

On the workstation, you said you used ethereal, when you made the request to get mail, did you see ANY packets from the workstation leaving to find a DNS server/wins server? From that same workstation can you telnet to port 25 on the mail server in question.

I would start simple, check dns resolution, do a nslookup from the workstation and see what you get for the hostname. Check connectivity, do a telnet to port 25 (assuming outbound smtp is what we are doing here), telnet to 110 if pop3 is what you are after.