1 Aug.

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!

 1 Aug.

Identity matters when getting Cortana to work on Windows 10

My wife is not a fan of the relationship I have with Cortana: she never forgets anything, knows my patterns, and I ask her to do things for me all the time – which are done without any complaint. With Windows 10 I am no longer restricted to only engaging with Cortana via my phone (and by extension my Microsoft Band) – I can now talk to her through my computer!

There’s a couple of roadblocks on this journey however. The first is well documented: if you want Cortana and live outside the US you need to set your region, language and speech to US. Only then will Cortana come to life.

The next one is your identity.

If you log in to Windows 10 using your Azure Active Directory / Office 365 credentials and try to enable Cortana you will receive this lovely text: “Cortana is disabled by company policy.”


Even if you have a MSA connected to your currently signed in account (that uses Azure Active Directory) it doesn’t work.

Doing some investigation I found that if you sign in using a Microsoft Account (MSA, formerly known as Live ID) then you won’t have this issue.

To confirm – I signed in on the same Azure Active Directory joined machine but with my MSA and was able to enable Cortana without issue.


Unfortunately there does not appear to be a setting (at this point) within Azure Active Directory to disable/enable Cortana. Hopefully Microsoft iterates quickly here and we can continue to log into our corporate accounts and have access to Cortana. In the meantime we will need to log in with our MSA’s and ensure that we configure our workplace under Accounts -> Work access.

UPDATE: It appears that the “issue” here is documented on the Cortana for Office 365 page under the section “Things to know before you use Cortana in Office 365″:
To use Cortana, people in your organization must be signed in to Cortana with their Microsoft account and must authorize Cortana to access Office 365 on their behalf. They can sign in with their Office 365 work or school account through Cortana’s Notebook.

This confirms that you need to be signed into Windows 10 using your MSA, not your AAD credentials. Hopefully this changes in the future.