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we are in a Hybrid environment and experiencing the following problem:
When a MAC Users mailbox is migrated over to Office365 and we setup a new Outlook 2011 Profile for theuser with automatic detection of settings we cannot get it to work. There is always an auth prompt that does not go away.
I tracked it down to autodiscover, which is pointing to our Exchange 2010 Hybrid Server.
The windows devices connect fine with autodiscover but the macs don't.
As a workaround i added an entry in the hosts file of the mac devices for autodiscover.ourdomain.com pointing directly to the public ip of autodiscover.outlook.com.
That does work without problems and there are no more auth prompts. But we would have to edit the hosts files on all our mac systems (50). Is there another solution that fits better without changing the host files?
Thanks for the feedback.
Based on my experience, in a Hybrid environment, the CNAME record for AutoDiscover is pointed to the on-premise mailbox server, so if you want to configure your Outlook by using AutoDiscover to connect to Office 365 outside of your organization, it will not work because CNAME record for Office 365 AutoDiscover does not exist.
Based on this situation, I would like to suggest you try to manually configure your Outlook for Mac by following method 3 from this KB. Otherwise, the workaround is what you did that you can add an entry into the host file to redirect to Autodiscover.outlook.com on every Mac computer.
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