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 From:  Jeff Buehler <jeff at buehlertech dot com>
 To:  m0n0wall at lists dot m0n0 dot ch
 Subject:  outlook -> exchange problem
 Date:  Thu, 02 Feb 2006 12:38:19 -0800
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.