Link to home
Create AccountLog in
Avatar of Malbys1
Malbys1

asked on

401 Unauthorized in Outlook Anywhere on SBS 2008

Hi all.

We've got an SBS 2008 box here with clients connecting using Outlook 2007 over Outlook Anywhere.

Whilst going about their daily business, users are randomly receiving a windows authentication dialog box stating "Connecting to remote.mydomain.com".  When entering the user credentials the box comes back straight away (suggesting an authentication failed event).  After clicking cancel a few times, the box disappears and the user is able to work as per usual.

Outlook appears to continue to work, so it's not affecting anything in particular, but the authentication dialog box keeps coming back every 10 minutes or so which is very frustrating to the users.

Taking a look at the IIS logs on the server, they're filled with a ton of 401.1 and 401.2 error messages, a small extract:
2010-12-31 00:21:37 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 13 62
2010-12-31 00:21:37 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 13 312
2010-12-31 00:21:37 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 13 62
2010-12-31 00:21:37 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 64 46
2010-12-31 00:21:38 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 13 62
2010-12-31 00:21:38 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 13 93
2010-12-31 00:21:38 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 13 78
2010-12-31 00:21:38 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 401 1 64 46
2010-12-31 00:21:42 192.168.0.30 POST /autodiscover/autodiscover.xml - 443 dja\kate 121.x.x.x Microsoft+Office/12.0+(Windows+NT+5.1;+Microsoft+Office+Outlook+12.0.6545;+Pro) 200 0 64 234
2010-12-31 00:28:02 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 192.168.0.1 Microsoft+Office/12.0+(Windows+NT+6.1;+Microsoft+Office+Outlook+12.0.4518;+Pro) 401 2 5 0
2010-12-31 00:28:02 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 192.168.0.1 Microsoft+Office/12.0+(Windows+NT+6.1;+Microsoft+Office+Outlook+12.0.4518;+Pro) 401 2 5 0
2010-12-31 00:28:02 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 192.168.0.1 Microsoft+Office/12.0+(Windows+NT+6.1;+Microsoft+Office+Outlook+12.0.4518;+Pro) 401 1 13 203
2010-12-31 00:31:36 192.168.0.30 GET /_vti_bin/sitedata.asmx - 80 - 192.168.0.1 Mozilla/4.0+(compatible;+MSIE+8.0;+Windows+NT+6.1;+WOW64;+Trident/4.0;+SLCC2;+.NET+CLR+2.0.50727;+.NET+CLR+3.5.30729;+.NET+CLR+3.0.30729;+InfoPath.2) 404 0 0 156
2010-12-31 00:32:13 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 192.168.0.1 Microsoft+Office/12.0+(Windows+NT+6.1;+Microsoft+Office+Outlook+12.0.4518;+Pro) 401 1 13 203
2010-12-31 00:33:26 192.168.0.30 GET /EWS/Exchange.asmx - 80 - 192.168.0.1 Mozilla/4.0+(compatible;+MSIE+8.0;+Windows+NT+6.1;+WOW64;+Trident/4.0;+SLCC2;+.NET+CLR+2.0.50727;+.NET+CLR+3.5.30729;+.NET+CLR+3.0.30729;+InfoPath.2) 403 4 5 218
2010-12-31 00:34:38 192.168.0.30 POST /Microsoft-Server-ActiveSync/default.eas Cmd=Sync&DeviceId=-----snip-------Translated=T 443 dja\dennis 114.75.78.16 - 200 0 0 810883
2010-12-31 00:35:46 192.168.0.30 POST /EWS/Exchange.asmx - 443 - 192.168.0.1 Microsoft+Office/12.0+(Windows+NT+6.1;+Microsoft+Office+Outlook+12.0.4518;+Pro) 401 1 13 203

Open in new window


I've taken a look at the IIS configuration and can't see any obvious problems, both Basic and Windows authentication is enabled on the sites in questions -- but I could easily be missing something due to the huge amount of sites and virtual directories SBS uses.

I'm not entirely sure if the problem lies with Outlook Anywhere, OWA or something else.

If this were a straight Exchange box I'd probably look at doing remove-OwaVirtualDirectory and set-OwaVirtualDirectory or similar, but I'm very aware of the fact that this is an SBS box and IIS has been configured for it rather than Exchange.  Given that users are actually able to work at the moment (although annoyed by the dialog boxes), I don't want to break things further.

Anyone have any suggestions as to where the problem may lie?
outlook.png
SOLUTION
Avatar of Olaf De Ceuster
Olaf De Ceuster
Flag of Australia image

Link to home
membership
Create an account to see this answer
Signing up is free. No credit card required.
Create Account
Check if you have host entries on the machine & if yes please remove it
SOLUTION
Link to home
membership
Create an account to see this answer
Signing up is free. No credit card required.
Create Account
ASKER CERTIFIED SOLUTION
Link to home
membership
Create an account to see this answer
Signing up is free. No credit card required.
Create Account
Avatar of Malbys1
Malbys1

ASKER

Hi sguinn100, I think you might be exactly right.  We were running Exchange at SP1 and that blog post exactly describes the issue we were having.

I've since upgraded to SP3 and update rollup 2.  Our users are currently out of the office (as you all should be!) so I can't easily verify that this has corrected the issue.  I'll report back in a couple of days as to how things are going.

Thanks all for your assistance.
Avatar of Malbys1

ASKER

It appears Exchange 2007 SP3 has indeed done the trick.

I should note that olafdc's suggestion of BPA actually highlighted the fact that we were using an old service pack and suggested that we upgrade which indeed would have corrected the issue had sguinn100 not found the exact cause of the problem.

Thanks all for your assistance.