Windows 10 quick tips: Get the most out of Cortana

Microsoft’s digital assistant Cortana was one of the major additions to Windows 10 when it first came out. But it was launched back in December 2015, and it’s changed quite a bit since then. Over the years, it’s had new features added, and then others taken away. Depending on which version of Windows you’re using, it may be integrated directly into the Windows Search box, or run as an entirely separate app.

No matter which version you use, though, it’s a very useful tool and can do a lot for you, including alerting you to upcoming meetings; searching your PC and the web; telling you about the weather, news, and sports; and a lot more.

To help you get the most out of Cortana, I’ve put together some of my favorite tips for using it — including using Cortana to manage your Google Calendar, send you reminders, and track packages and flights.

But because Cortana works very differently depending on what version of Windows 10 you use, I’ve separated this article into two parts — one that covers tips for Cortana using the latest version, the Windows 10 May 2020 Update (version 2004), and the other with tips for the previous two versions, the Windows 10 November 2019 Update (version 1909) and the Windows 10 May 2019 Update (version 1903). Use the table of contents in the left margin or below to jump to the appropriate section for you.

(Note: This article assumes that you’re already familiar with the basics of Cortana. If you have Windows 10 version 1903 or 1909 and want help getting started, see the “Cortana and search” section of Computerworld’s “Windows 10 cheat sheet.” If you have Windows 10 version 2004, see the Cortana section of our Windows 10 May 2020 Update review.

Tips for Cortana in Windows 10 version 2004

Before we head into the tips for the Windows 10 version 2004, we should cover a bit of background. Cortana used to be integrated in the Windows search box: Whether you performed a search by speaking or typing, the results were delivered in the Cortana pane. But with last year’s Windows 10 May 2019 Update, Microsoft separated Cortana from the Windows search box. And in the new Windows 10 May 2020 Update, Microsoft went ever further and turned Cortana into its own app that works like any other Windows 10 app, including running in a resizable window that can be moved around the screen.