Microsoft today updated the web version of its email client in Office 365, Outlook on the web (formerly Outlook Web App), with address book improvements and flight events in your calendar. The former focuses on learning who you send emails to and helping you avoid mistakes while the latter automatically adds flights to your calendar based on confirmation emails.

This will be a rolling release with a lot of timing nuance. The address book improvements will start rolling out in mid-January to Office 365 First Release customers and then to a broad rollout by early March. Outlook for Android, iOS, and Windows will get the address boot improvements in the first half of 2016, while the Mac app doesn’t have a timeline yet.

Automatic flight confirmations will roll out in early January 2016 to Office 365 First Release customers and the new currently in preview, with a broad release in March 2016. Because events are stored in your calendar, they will automatically show up in all versions of Outlook (Windows, Mac, Android, iOS, and Windows Phone) that are connected to your Office 365 or mailbox.

With all that out of the way, let’s dive into the details of the features.


When you place your cursor in the To: or Cc: line, Outlook will now show suggested contacts based on your usage. “These are the people you’re most likely to email based on who you’ve been communicating with recently and most frequently,” Microsoft explained.

Next, Outlook has brought its spell checker to help with names. Outlook will now show you names of people you email most frequently, even if you spell their name wrong (Jon versus John, Kathryn versus Catherine, and so on).

Lastly, if you frequently send emails to the same set of people (Harrison, Matt, and Neil), then whenever you email only Harrison and Neil, Outlook will ask, “Do you also want to include Matt?” Microsoft promises that Outlook will only show this suggestion when it is “highly confident” that you want to add Matt.


The second feature is actually called “Events from email” because Microsoft doesn’t want to stop at just flight confirmations. But for now, Outlook will add flight confirmation emails from Expedia, Southwest Airlines, American Airlines, United Airlines, Delta Airlines, and Alaska Airlines directly to your calendar. More providers will be added on a rolling basis, as will other types of events beyond flights.

This feature is great because it doesn’t require any copying and pasting or dragging and dropping — it’s all automatic. The event is blocked off on your calendar, and you see the flight number, destination, airport, and original email along with an automatic reminder three hours before your flight. You can turn this on and off by clicking Settings (gear icon), Options, Calendar, and then “Events from email.”

Google has been working on this type of integration between Gmail and Google Calendar for a while now. Microsoft’s addition is long overdue, but better late than never.