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Exchange over site-to-site VPN: can ping server local Ip but cannot send/recieve mail

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Exchange over site-to-site VPN: can ping server local I... - 24.Sep.2009 4:07:49 PM   
csialbany

 

Posts: 4
Joined: 24.Sep.2009
Status: offline
Hello,

We have a main office with a machine running small business server 2003 w/ exchange. We have set up a site-to-site vpn connection to a remote office. We cannot currently send/receive mail from outlook exchange accounts on the remote computers. However if we disconnect the site-to-site vpn and connect from the remote computers to the main office server with the microsoft vpn client we can send/recieve mail without a problem.

The main office has a subnet of 192.168.1.0. The exchange server has 2 NIC's. The IP of the server's internal LAN NIC is 192.168.1.13. The IP of the server's WAN nic (connects to router) is 192.168.1.103. Finally the exchange server is identified as "mailserver.ourorganization.local"

The satellite office has a subnet of 192.168.2.0.

With the site-to-site vpn connected we have a computer at the satellite office setup to use 192.168.1.103 as its DNS server. From this remote computer we can ping the exchange server at 192.168.1.13 with no problem. When setting up the users account in outlook we enter 192.168.1.13 as the server and it automatically updates to "mailserver.ourorganization.local". This leads me to believe the remote computers are communicating with the server (as is verified in the router logs).

When pinging mailserver.ourorganization.local the address resolves to 192.168.1.103 but the ping times out.

Not sure where to proceed from here, any help is greatly appreciated.
Post #: 1
RE: Exchange over site-to-site VPN: can ping server loc... - 26.Sep.2009 7:20:45 PM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
This is going to sound negative, but hang in there and I'll explain.

Being able to resolve a name to an address doesn't necessarily mean that it is coming from DNS.  There are other ways to obtain that information.  A hosts file can contain static information, and systems can cache name information (DNS cache).

Not getting ping responses does not necessarily mean that a route is broken.  Ping requests and acknowledgements are carried by ICMP, just another protocol that is subject to restrictions like anything else.  It could also mean that the route in one direction is fine, and in the return direction is not configured properly.

I only bring up these two point because while your troubleshooting techniques are valid, your conclusions are not the only ones possible.

That being said, let's talk about your symptoms.

Since Outlook isn't able to connect, it seems that either there is a networking issue (physical or logical), or a connectivity issue (ports).  Outlook communicates with Exchange via MAPI.  Read this article for information about the ports used by MAPI.  To test whether your client computer can "see" the Exchange server, you might also test using Outlook Web (OWA).  Open a browser and point to http:\\servername\exchange.  If you either get OWA to open or are prompted for a username/password, you have verified the networking via port 80.  In that case, check anything between the workstation and server capable of port filtering.

You may need to check your routing equipment between the two sites to make sure the address ranges on either side are routable.  What does that mean?  Make sure the same information is used to describe the subnets everywhere they are configured.  In other words, is the network 192.168.1.0 always paired with the subnet mask 255.255.255.0?  What is the default gateway for systems on either side?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to csialbany)
Post #: 2
RE: Exchange over site-to-site VPN: can ping server loc... - 2.Oct.2009 8:42:49 AM   
csialbany

 

Posts: 4
Joined: 24.Sep.2009
Status: offline
Thanks for the quick reply. I am able to access the OWA by navigating to 192.168.1.13/exchange. However navigating to mailserver.ourorganization.local/exchange fails (pointing to DNS issues again).

I have double checked the subnets and they all are matching.

In regards to DNS caching, I have run ipconfig /flushdns on both machine.

(in reply to uemurad)
Post #: 3
RE: Exchange over site-to-site VPN: can ping server loc... - 2.Oct.2009 9:03:51 AM   
csialbany

 

Posts: 4
Joined: 24.Sep.2009
Status: offline
I just checked the DNS record on the server after restarting and it was reset to 192.168.1.103. Thanks for the advice, sorry for the red herring!

(in reply to csialbany)
Post #: 4
RE: Exchange over site-to-site VPN: can ping server loc... - 2.Oct.2009 9:18:25 AM   
uemurad

 

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline
Does that mean you still have a problem, or have you resolved it?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to csialbany)
Post #: 5
RE: Exchange over site-to-site VPN: can ping server loc... - 2.Oct.2009 9:23:01 AM   
csialbany

 

Posts: 4
Joined: 24.Sep.2009
Status: offline
Yes, I reset the record to point to 192.168.1.13 and the outlook clients at the remote site can now connect to the server over the site-to-site vpn. Thanks for your advice Dean.

(in reply to uemurad)
Post #: 6

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