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There is a bizzare problem with one, specific user.

Server: Windows 2003 TS, Outlook 2007 SP3 Exchange 2010 SP1

There was a user, let's say User01 with Exchange Mailbox. For some reason (unrelated to Exchange issues - before everything was fine) i needed to delete this user from active directory.

This, of course, led to disconnection of mailbox in Exchange Server. Then, i recreated the user, with the same account name and generally same user details. I removed however, all the roaming profiles before, so the new user got new profile. I believe, recreation of account also led to creation of new SID for this user.

After, i reconnected Exchange Mailbox to the new user account. This has worked flawless.

Now, i tried to setup an Outlook 2007. And i failed. Configuration fails with the message: "Outlook cannot log on. Verify you are connected to the network and are using the proper server and mailbox name." Basicly, Outlook is not able to discover username or connect to exchange.

However, autodiscovery feature works perfectly fine for all other users on this server. I tested MAPI connection (with cmdlet), works fine. I checked permissions (as far as i know) and i found nothing unusuall on the AD user object. Servername is correct, for all other users configuration this works fine with autoconfiguration. There are no events in eventlog, connected to these events. Generally i see no errors or even warnings (also in security). I have also tested this on other TS Servers, and the same issue happens, so i don't think it's server related.

I believe the problem is connected somehow to the AD user object. Maybe even some rights. Any tips what could i test further?

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When you reconnected the mailbox, did you use "matching user" or "existing user"? –  Cheekaleak Oct 30 '13 at 13:29
    
Existing user, then i choose from the list this specific user account. –  Tomasz Szkudlarek Oct 30 '13 at 13:32
    
Ok, what happens if you try to log into the mailbox from OWA? –  Cheekaleak Oct 30 '13 at 13:33
    
OWA seems to works just fine, even if i open it from the same TS server where i setup the Outlook, with this problematic user logged on. So, it's rather configuration related issue? There shouldn't be anything wrong with permissions, i assume? –  Tomasz Szkudlarek Oct 30 '13 at 13:46

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