Outlook 2016 connecting to Office 365 mailboxes?

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I am in the process of preparing 100 student computers. They are all being imaged from a MDT 2013 server onto Surface Pro 4, they are identical other than the computer name and the user logging into them. I have done 12 so far in 2 groups of six. 1 in each group of six connects fine and Outlook builds profile and everything is great. 5 of the 6 for a total of 10 so far get stuck at this screen:

Outlook 2016 to Office365 clean.png


I have tried the Remote Connectivity Analyzer as well as Microsoft Support and Recovery Assistant for Office 365 and both say everything is great and should be working. Also some do work. They are all sitting on table next to each other connected to same switch. I can setup Windows Store for Business, OneDrive for Business with these same accounts without issue. I am really pulling my hair out here trying to figure this out.

The same thing happened with some of my Faculty and I just did it later and it magically worked? I would however like to not have to boot up and login these machines again before deployment on chance it will work.

Any suggestions or help greatly appreciated. Thanks.



1 Reply

I have figured out the problem. These are Surfaces as I said. While I am configuring them to save myself time I use the Windows Mobility Center to turn on Presentation Mode to keep the machines from falling asleep. That causes Outlook to not configure properly. I tested it over and over after I figured it out and can replicate it everytime. I have no idea what presentation mode has to do with configuring an Outlook profile though. This is some odd bug for sure.