Terminal Server issue with outlook connecting to exchange online

I have setup up a server 2012 R2 for terminal services for 3 users, i have installed all licenses required.

We have installed Office 2016 Standard Volume Licensed Edition

The issue i am having is connecting outlook to exchange online and it hangs and doesnt connect up to the server.

I can log on from the server to the webmail with no issues.
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Vasil Michev (MVP)Commented:
You are not giving us much to work with... Does it hand when configuring the profile or when launching Outlook (after the profile is already configured)? Are you using Online or Cached mode? Have you confirmed that all relevant URLs and IPs are allowed in your env?
techno106Author Commented:
Yes sorry, when i am opening outlook and setting up the account and click next to set the profile up it just sits there and fails to connect to exchange. It sits saying connecting to exchange but never does.

The profile just wont configure.

I have also tried to set this up manually with the settings required and it does the exact same thing.
Vasil Michev (MVP)Commented:
Try querying the Autodiscover service from the local machine by holding the CTRL key and right-clicking on Outlook's icon in the tray. Enter the username and password, clear the two GuessSmart checkboxes and run the test, then monitor the status on the Log tab. If it fails, post the sanitized results here.
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Jackie ManIT ManagerCommented:
The hang is in relation to your deployment setup.

By default, Outlook 2016 will use cached exchange mode. However, as your deployment is on RDS, there might be not enough disk space or I/O’s are not sufficient. Besides, your user should have a large exchange mailbox in exchange online, the cache will start to grow in size when you setup the Outlook profile.

When the cache or the I/O reaches its limit of your RDS, Outlook will just hang up.

In order to fix the above, you can use Office Customization Tool or in Group Policy to change the default mode to online mode. The drawback is slow performance.

Or you can seup a network share within RDS to store the ost file and install Windows search on the server which provide the network share and point the ost file to that network share. You can still use cached exchange mode.

techno106Author Commented:
Please see error for autodiscover
Vasil Michev (MVP)Commented:
It's normal for AutoDiscover to fail on some methods, the important pats it that it needs to success on the HTTP redirect one (the CNAME). You havent included that in your screenshot.
techno106Author Commented:
I have found a solution that has fixed my problem, the below link is  a tool which sets the account up for you. Jackie Man was on the right track with setting it up as outlook in non-cached mode. For some reason i couldnt change the settings for this to work.

Once i ran the tool it set the profile up for me.


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techno106Author Commented:
The tool works to get your outlook profile up and running.
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Windows Server 2012

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