Just posting this here in case anybody else has any ideas. I am configuring a script to setup Outlook 2003 on first login using a .prf file. I am setting it up to work with an RPC over Https client I got all of that working fine. To get this to work we need to go through a proxy in order to get through the firewalls correctly. The issue I am having involves the proxy settings in internet explorer. If I leave the bypass proxy for local address option unchecked, the setup works as I expect and we have the whole thing done in under 45 seconds. If I check that bypass proxy option the setup takes over 4 minutes eventually timing out. If I rerun it again manually it eventually finished configuring itself. The issue is we need to leave the Bypass option on for other programs to work correctly. I have seen reports of this before with Microsoft in this knowledge base article here http://support.microsoft.com/kb/331320 That sounds very much like the symptoms I am having the only issue is I am on XP Sp3 and that patch was added in Service pack 2 so I cannot install it here. It seems to be almost like a timeout issues, like the setup tries and connects to the local exchange server through a non RPC connection and we need to wait for it to timeout after 3 minutes or so before it tries the RPC connection to connect to it. Has anybody experienced this before or does anybody have any ideas on this? If I figure it out I will be sure to post the answer here if the answer has not already been posted. I have been racking my head about this a good part of the day, think I will head home and sleep on it for now, thanks in advance for any insight into this matter.