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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Ron Cohen
The Netherlands
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