Outlook 2011 Errors

When I first tried to setup my Outlook 2011 to connect to my SBS server running Exchange 2007 it appeared to setup first try. IT connected to the mailbox and downloaded all my emails, calendars, tasks, etc. However I noticed that Outlook hung a bit and didn’t want to close. So then I rebooted the mac and then Outlook wouldn’t connect to the server anymore and kept prompting for username and passord. Tried recreating the account and still wouldn’t connect.

So I went searching the internet for ideas. The most common suggestion was to rebuild the virtual directories for a few folders. I tried the commands from the shell as I found and just getting one errror after another that the specified directories didn’t exist. So reasoning that reboot would have I similar effect, I rebooted the SBS 2008 server. After that Outlook on the Mac connected instantly again and was functional. Over the next 20 minutes using it I noticed the same degradation in Outlook and after waking up the Mac from sleep mode I was back to being prompted for username and password again. Rebooted the server again and instantly Outlook connected. Not really a good fix to reboot the server continually so I went looking for another fix.

I found a link to  solution that no one else was giving but made sense – http://www.petri.co.il/forums/showthread.php?t=45093  (thank you)

I fumbled around with those instructions a bit but was able to enable the kenel mode authentication on all the virtual directories and Presto! instantly Outlook was working as it should. Outlook continued to work fine through out the rest of the day and I never had to reboot the server for that issue so this seemed like the fix. I appreciated the help but was worried I would never track down that answer if I needed again so I posted it here and below added some screen shots to make it easy to follow.

Step 1:

Connect to the Server and start IIS Manager


The IIS window then opens

Step 2:

Click the + sign next to the servername and then again next to sites


Select SBS Web Applications



Then select Rpc

In the right hand window double click on Authentication

Right click on Windows Authentication

select Advanced Settings


Check the box for Enable Kernel-Mode Authentication


Now complete the same process for all the required folders highlighted below.


Once completing this process your Outlook 2011 users should have no problem connecting to the exchange server.