Challenges connecting Cortana to Office 365

In my previous post I spoke about the fact that Cortana only appears to work on Windows 10 if you are signed in with a Microsoft Account.

Now that I had this working I was eager to connect Cortana to Office 365 and get some valuable insights and interactions.

Our first step is to access Cortana’s notebook:

 

Once here we see that Office 365 is set to “off”, so let’s set that to “on”:

 

We’re now prompted to connect, and are presented with the fact that Cortana will now have access to things she previously didn’t have:

 

Now let’s authenticate to Office 365:

 

And now we… wait what?

 

I went to the Office 365 portal to find that Cortana was turned off (I could have sworn it was set to “on” previously).

I turned Cortana on (again, I think):

 

Then I went through the process of connecting again and presto!

 

It is important to note that for Cortana to work you will need to make sure the Windows 10 Mail and Calendar apps are also connected to your Office 365 account.

Now let’s see what happens from here!

 

UPDATE: It is confirmed via Microsoft KB 3086254 that Cortana will not work with Office 365 if you are signed in using your Azure Active Directory account.