XP, Outlook Anywhere and TMG Configuration

This is my first post so I thought to start with a strange case that I was working on last week.

Customer environment as follows:

– Exchange 2010, with CAS configured properly for Outlook Anywhere.

– TMG configured to publish Outlook Anywhere.


Problem Symptoms:

– Outlook Anywhere on Windows 7 is working fine.

– Outlook Anywhere on Windows XP with SP3 is not working for both Office 2003 and Office 2007.

If configuring Outlook for the first time it will hang after asking for the user name and the password, same if Outlook configured before, once opened it will ask for the user name and password and then not responding.



Testing from Windows 7 proofs that the configuration is ok, also testing Outlook Anywhere from Internet Explorer is working fine (https://mail.customer.com/rpc/rpcproxy.dll).

The key in identifying the problem was testing XP from the internal network and everything worked fine, then it should be something in TMG publishing rule.



on the first look the rule looks fine, and also is working from IE and Windows 7, checking the rule on the second time and check the following snapshot:



The Load balance Mechanism first was selected to be “Cookie Based”, of course Outlook Anywhere should be configured as Source IP, once changed to the right configuration as the snapshot above everything now is working fine.


My conclusion for that strange behavior that Outlook 2003 and 2007 not supporting any cookies (only Outlook 2010 supports “Outlook Session” Cookie), it seems that Windows 7 is smart enough so it’s dropping the cookie and ignore it, for XP it can’t understand the cookie and Outlook hang with no response.