Windows 10 and Office 365 – First Impressions

So I spent my Sunday upgrading to Windows 10. I already have my surface on Windows 10, but I wanted to walk the experience of setting up Windows 10 and getting right on to Office 365 for the full single sign on experience. The upgrade was flawless, I even let Windows just keep my files and scrap my programs which gives me a slightly cleaner upgrade. I was never a fan of straight upgrades of on operation system, but Microsoft has been doing an awesome job and I have to say, I am sold.

Joining Azure AD

The first step in getting the single sign-on experience with Windows 10 is joining your computer with Azure AD. Traditionally there have been two options available for a Windows Computer professional and above

  1. Workgroup (default)
  2. Join Domain

Since Windows 10 is more of a cloud centric OS, Microsoft has included the option to join Azure AD which essentially uses the cloud and your Office 365 identities to authenticate instead of an on-premise domain.

Join Azure AD

From there I logged out of my profile and tried to create a new profile based on my Office 365 credentials. Everything kind of spiraled downhill from there. I got some errors around authenticating my user which I was eventually able to skip. Once into my profile with my Office 365 credentials I was pleasantly surprised that Windows Mail was already configured.

I then went to configure Outlook. I had to enter my credentials manually, I was hoping they’d be picked up automatically…Once I entered everything, it did work…just not the out of the box experience I was hoping for. One interesting bit was it requesting for my domain creds for Azure AD, which it uses what looks like Azure AD as the primary domain.

setting up Outlook

I had the same experience with Skype for Business. I launched it, and it wanted me to provide credentials. Again I was hoping for the single sign-on experience.

One Drive for Business wants my library URL, which I guess is forgivable since you could have many.

All in all, it isn’t the experience I was hoping for. Once everything is setup, it’s fine…but I could have done the same thing with a  normal account.

I will keep plugging away and see what I come up with.




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