I blogged about this issue a couple of weeks ago. Initially, the solution I described in the article worked for me on my two computers running Windows Vista.
Recently I had a need to do a similar setup on different machines, running different OS versions. Unfortunately, it did not work.
After googling for a while I found a solution and I started using a free Outlook AutoLogin tool from Gabriele. I never had a problem since. The tool can be downloaded at his website http://www.mondada.net/gabriele/autologin. It works with Outlook 2007 and I tested it on Windows Vista as well as XP.
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