Microsoft has released a tool, called SARA, that can help diagnose issues with Office 365. Currently, its configured to help setting up Outlook with Office365.
SARA is the Support and Recovery Assistant for Office365, and can help diagnose issues from you entering the Office365 account, and then using the Support topic options to get help with. SARA is an on-demand application, so it only needs to be used when there is a problem indicated. Of course, access to the Office365 tenant will be required to use this tool! Its early days for SARA as I write this quick blog,, but, I guess it would be useful to keep an eye on this tool, as Microsoft continues to upgrade it to help support issues with other products in the Office365 suite.
Check the below video for more information, and download link is below the video.