Simple IT made complex

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Posts Tagged ‘exchange 2010

Outlook 2011 not working with Exchange 2010

with 69 comments

A colleague of mine was setting up a customer for Exchange 2010. Everything was set up like it should be, Outlook 2007 and Outlook 2010 clients worked like a charm. This customer also has a few Macs running Office 2011, where Outlook unfortunately refused to do anything (literally). When he put in the information for the Exchange server, nothing happened. It would just sit at an empty mailbox, no connection errors, no authentication errors, nothing. Let me be honest and say that at my company, we’re not exactly good when it comes to Macs, we’re actually quite horrible. Anyways, we struggled a long time as we kept getting no feedback on the process from the Mac. The solution? Keep reading!

The solution

When we finally found the solution, it was a fairly basic one. Outlook 2011 doesn’t use MAPI, it relies solely on EWS (Exchange Web Services). When we tried to browse via a browser on the Mac, it wouldn’t prompt for any credentials, just show a blank page, where a Windows computer would actually show something useful. Then we checked the authentication allowed for EWS in IIS. It was set to allow Anonymous Authentication (this is required by the Exchange server) and Windows Authentication. Obviously you need to authenticate to pull anything useful out of this service, and, for perhaps pretty obvious reasons, the Mac wasn’t using Windows Authentication. We enabled Basic Authentication and it started working immediately on the Mac. If you want to make sure it’s updated fast, do a iisreset from a command line.

These images should tell you everything.

Fire up your IIS manager, find EWS (in this case in the Default Web Site), open Authentication.


Enable this bad boy and you're set. Do a iisreset if you're impatient... like me.

There’s a lot more to this story than just the above steps, it felt as an uphill battle the entire time, but I won’t bore you with all the troubleshooting we did (even though I already did a little).

Written by dryerr

November 10, 2010 at 21:44