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Repeated outlook username prompt after 10 minutes...

hillgreg asked
I am currently setting up a SBS 2008 server.  I can connect to exchange from an enrolled computer, and from owa without problem.  I have installed a certificate with the names
remote.docgreg.com, autodiscover.docgreg.com, DOCGREG-SERVER.docgreg.local, and docgreg.com.
Initially, when connecting to the server using RPC (outside the network) I can connect to outlook.  After about 10 minutes, however, I can no longer do so.  I get the prompt for username and password to log onto DOCGREG-SERVER.docgreg.local and it is repeated indefinitely.  Rebooting the server resolves the problem, for about 10 minutes.
There seems to be something that is being overwritten somewhere after a restart.  I would appreciate any advice as to where this might be.
Of note, when I do a remote desktop, I get a certificate error (shows the self signed certificate), although when checking the server under terminal server, it shows the proper godaddy certificate I'm using.  Maybe this cert is being changed after 10 minutes?
I'm also questioning if the authentication method is being overwritten after some time.  What should the authentication methods be?  And under what web service?
Watch Question

What version of Outlook and have you installed Exchange 2007 SP2 on there? Pre SP2 is known to have password prompting issues.

Do you get the same password prompt when using Outlook from inside the LAN?


It appears that upgrading to SP2 did fix the problem, though I also had to re-install the ssl certificates.  Shame that SBS 2008 is still being sold with this problem, as logging into Exchange remotely is a common need.

Thanks for the update and the points.
I just found this article and wanted to keep it updated.

I just installed SBS 2008 Premium R2 84-bit. It was indeed a migration from SBS 2003. I went through the BPA for SBS 2003 Migration to SBS 2008 until it was 100% error free. The migration went 100% flawlessly (1st time of 4 on this same migration type). wait...

I go to open Outlook 2007 and I was prompted for logon information. I entered it over & over in many fashions but it wouldn't take the logon info. I clicked Cancel 3 times and email rolled in. The logon screen repeats appearing in a few minutes. I just click Cancel 3 times & all is well. I checked 2 other users' Outlook 2007 and it was the same. ALL 3 clients were running XP Pro & Outlook 2007 with all the latest updates.

What, oddly, fixed it for me was this article I found... http://exchangemaster.wordpress.com/2009/12/21/sbs-2008-and-ru3-and-outlook-repeat-login-prompt/ . **when the article shows (in Step 4) "windows Authentication -> Disable -> enable," they actually mean just toggle it** I didn't Disable, Apply, Enable, Apply, Restart. I simply Disabled, Enabled, OK )on all 3 items the article talks about, and then Restarted.

I tested 2 of my original 3 test clients and they were NEVER prompted for logon info. Not when I opened Outlook. Not after 20 minutes. The weird logon prompt was gone!

Since I want to be current with SPs from the get-go, I just installed of SP3 for Exchange 2007 on SBS 2008 Premium R2 64-bit. I followed the advice to run from an elevated command prompt, which I found in article http://wintivity.wigital.net/blog/2010/01/11/exchange-2007-sp1-update-rollup-9-fix-outlook-pop-up-sbs-2008/ saying this was the only way to get Rollup 9 (a just-previous-to-SP2/post-SP1 patch) to install correctly. I followed article http://support.microsoft.com/kb/982423 and downloaded SP3 for Exchange 2007 (most current at the time of this post), then ran it from an elevated command prompt. I did NOT install Forefront Security (we use Trend Micro's WFBS online scanning combined with their network-managed piece(s) and a brand new SonicWall TZ210 w/CGS).

The clients continued to work after installation of SP3.