Outlook 2010 profile corruption problem?

Howdy all,
So I have a Windows XP Virtual Machine (within OSX), running Office 2010, and using Outlook 2010 to connect to my new Exchange 2010 server over Outlook Anywhere.

When I first setup Outlook's mail profile, I successfully connect via Auto-discovery and the mailbox correctly caches on my machine.
Then, for some reason, about a day later, my Outlook 2010 sits trying to connect and simply wont - Constantly asking for my password, like it was wrong (but it isn't).

To get it going again, I have to delete the Outlook 2010 Profile, and recreating it - Rinse and repeat every day for the last 4 days so far, so I'm worried other users have the same problem, as we've just upgraded them to Office 2010 as well (It's the weekend so I can't check with them yet), but regardless - I have this crazy problem.

Everything is perfect with the Exchange 2010 server, I don't have any problems with Outlook 2011 for Mac, iPhone Sync, Outlook Web App - They all connect and remain connected perfectly.

Any thoughts?
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Can you double-check if your certificate issued-to name and the MSSTD value on the Outlook profiles are having the same values?

> During the time of the issue, when you connect this profile from the LAN (locally) to the exchange server...do you see the same issue?

>> Any other users affected?
If the same mailbox is configured on another machine...is that working fine?
GwummAuthor Commented:
Yes, certificate name and MSSTD correctly match. All other aspects of the SSL is correct as well.
I'm not sure about LAN to be honest, this server is colo'd (100% remote).
Also not sure about other computers as yet, although one other user has mentioned the same problem (i'm just not sure if it's widespread).

That patch doesn't seem relevant? If it is, which part am I missing?
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Why don't you install that patch and find out if your problem is resolved? Worst case scenario is that the patch doesn't work, but at least will know what version of Outlook you are on...
GwummAuthor Commented:
I just tried it, and unfortunately no success - In fact, I'm not sure if it's related, but I now can't even recreate the Outlook profile by connecting initially - It's simply acting as if the password is wrong, but naturally I can still connect with the same password from everything else.

Any other ideas?
Time to test outlook autoconfig:
With outlook open, hold down CTRL key and right click on the Outlook icon in the bottom right hand side of your screen, then on the popup menu select the "Test Autoconfiguration". Select that, enter valid credentials and select the "autodiscover" option only and test.
And see what URLs are being returned and any error codes.

Since you are using Outlook Anywhere, I take it that you are using Outlook over an Internet connection? Have you performed the Outlook Anywhere test from www.testexchangeconnectivity.com?

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GwummAuthor Commented:
Winning! - We might have it, but I'll have to wait 1-2 days to make sure.

After applying the patch, I actually couldn't connect at all - Even after trying to recreate a profile, I actually couldn't even create a new profile. So, I took your 2nd part advise and tested via www.testexchangeconnectivity.com - I always use this, why didn't I this time (/slaps forehead).

Sure enough it had the following error:
The certificate common name domainname.com doesn't validate against the mutual authentication string that was provided: msstd:mail.domainname.com

Rather annoying, when both names are part of the SSL certificate. But after seeing this, I ran the following command to change the msstd to match the common name:
Set-OutlookProvider EXPR -CertPrincipalName:"msstd:domainname.com"

Immediately after I was able to connect perfectly, but I will provide an update in 1-2 days, assuming no further problems occur.
GwummAuthor Commented:
Yep, all good and working now!
Cheers :)
GwummAuthor Commented:
Pointed me in the right direction.
Thanks for the points. I am glad it is working for you now.
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