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We've got a Server2008R2 functioning as a terminal server.

Users attempting to open Outlook10 on this server get stuck at "Loading Profile"

Sometimes a username\password field will come up after about 25-30 seconds, filling it out correctly can result in Outlook opening properly 20 seconds later, or a "Server not found, work offline?" window. Sometimes hitting Retry will force Outlook to open.

Sometimes rebooting the server fixes the issue, sometimes it does not.

Any help?

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Is the outlook on the terminal server set to use cached exchange mode? Can you turn it off and see if you get the same results? –  Nic Young Feb 20 '12 at 17:09
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I seem to remember reading somewhere that cached exchange mode should not be used on terminal servers, all of our users should be using online mode –  wooz Feb 20 '12 at 17:33
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Ok, there are a couple of things I would check. is outlook anywhere enabled in exchange? Have you tried wiping out the user profile and re creating it? –  Nic Young Feb 20 '12 at 17:51
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Outlook Anywhere is enabled, and works like a charm internally and externally, just not on the TS. Wiping out a user profile doesn't seem to have an effect. I've created a few test users and had Outlook autodiscover their settings on the TS, I've also manually configured Outlook, same result. –  wooz Feb 20 '12 at 17:54
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Do you mean from the exchange farm? I haven't tried that, I suppose I could give it a go late-night tonight, I've got a bunch of users working from home using Outlook(not through the TS, just locally from their laptops) so I can't really test it right now. –  wooz Feb 20 '12 at 18:09

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