The DNS is resolving properly, so a ping of the Exchange servers FQDN 
from the workstation results in the proper resolution to the Exchange 
server IP.

Ron Cohen wrote:

> Did you try putting the exchange server's name in your remote pc's 
> hosts file or is there a DNS entry on your pimary (not exchange) 
> server that points to your exchange server on the other side of the VPN?
>
> Jeff Buehler wrote:
>
>> Hi Everyone -
>>
>> I have a strange problem involving Outlook connectivity problems to 
>> Exchange over a m0n0wall <-> m0n0wall ipsec VPN
>>
>> 1. Network of 20 or so workstations connected like this:  workstation 
>> -> switch -> m0n0wall -> internet.
>> 2. There is a domain controller also connected to the switch that 
>> provides primary DNS and Active Directory
>> 3. There is another domain controller, this one with the Exchange 
>> server, on a physically separated network, with another m0n0wall in 
>> front of it.
>> 4. each of the two networks is connected via an ipsec VPN that is 
>> working great.
>>
>> All workstations that predate the switch to the m0n0wall vpn on the 
>> same network are working fine, but when we connect new workstations 
>> they have trouble connecting to Exchange from Outlook.  It is very 
>> slow (5 minutes to connect) and intermittent.  The new workstation is 
>> working well in every other respect - no dropped packets, solid ping, 
>> great browser access, and so on.  Only the Outlook (and Mail control 
>> panel) are having this problem, and it is very severe (sometimes it 
>> just fails, usually it sits there for 5 or more minutes and finally 
>> connects, sort of).
>>
>> Any ideas on this one?  I am inclined to simply despise Microsoft 
>> even more than I do and chalk it up to a problem of theirs, but I 
>> thought I would check and see if anyone else has seen anything 
>> similar to this ...  I'm not even certain how to debug it with the 
>> Microsoft tools.
>>
>> Thanks,
>> Jeff
>>
>>
>>
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>