Microsoft’s Cortana gets new chat-based experience, Briefing email, and Play My Emails updates

Cortana’s new gig as an office assistant for work finally kicks off with the Windows 10 May 2020 update.

When you purchase through links on our site, we may earn an affiliate commission.Here’s how it works.

What you need to know

What you need to know

Coinciding with the Windows 10 May 2020 update, Microsoft is finally pulling the covers off the new chat-based Cortana experience. Additionally,Play My Emailsis getting new features and Microsoft 365 Enterprise users can now receive an Outlook “Cortana Briefing” email, which provides personalized “intelligent, actionable recommendations” for documents and meetings for the day.

All of this is part of a broader shift in Microsoft’s strategy around Cortana, moving it away from a consumer-focused do-it-all smart bot, to onefocused on productivityaround Microsoft’s core Office suite. These are some of the first results of that effort.

Let’s talk, or not

Cortana chat-based experienced

Cortana chat-based experienced

Those who are a part of the Windows 10 Insider program have hadthe new Cortana experience for months now, but it is officially coming for regular users in the Windows 10 May 2020 update.

Situated as a pinned app outside of the Windows Search bar, the new Cortana ditches many of the previous iteration’s Alexa-like functions such as skills. Andrew Shuman, Corporate Vice President of Cortana, tells us that the work involved with removing Cortana from the OS was monumental in scope. A lot of this is due to ensuring Cortana fully observes “Office 365’s enterprise-level privacy, security and compliance promises as laid out in theOnline Services Terms.”

While it is still early days, the new Cortana has the following abilities:

When connected to a Microsoft 365 account, users can ask Cortana things like “Am I free at 9?”, “Find time with Nestor to talk about the budget,” “Join my meeting,” and “Remind me to review expenses every Friday at 3 PM.”

Get the Windows Central Newsletter

All the latest news, reviews, and guides for Windows and Xbox diehards.

But Shuman tells us a lot more is on the way and that his team has “many great ideas in the pipeline.” Much of that does include expansion to other markets, too, especially ones where Microsoft 365 is used predominantly. FromMicrosoft’s blogon today’s announcement:

In the coming months, with regular app updates through the Microsoft Store, we’ll enhance this experience to support wake word invocation and enable listening when you say “Cortana,” offer more productivity capabilities such as surfacing relevant emails and documents to help you prepare for meetings, and expand supported capabilities for international users.

There is potential for Cortana to become a real productivity enhancer based on Microsoft’s premium work experiences for students, consumers, and business users. Cortana already integrates with Outlook, To Do, and the AI is a knowledge graph from Bing with deep reaches into other products, including PowerPoint.

Windows 10 has seen a massive surge in usage during the current pandemic, and Microsoft sees AI and Cortana as eventually playing a significant role in that market shift.

You have 42 new emails …

Play My Emails gets meeting scheduling ability

Microsoft’s Play My Emails feature (see Microsoft’s blog post), currently available in iOS and coming soon to Android, lets users listen to their focused inbox messages with headphones or through their car’s Bluetooth.

Cortana powers the experience. It reads back your emails, but in natural language, letting users know some images can be viewed later, while also skipping nonsensical things like shipping numbers. Users can also reply if usingSurface Earbudsor Surface Headphones 2, delete emails, or skip all hands-free.

Starting today, users of Play My Emails get the following new abilities:

For those with Android phones, or those waiting for Microsoft’s Surface Duo, the Play My Emails feature will be available on that OS “in the coming weeks.”

Here’s what you need to know

The skinny on Cortana Briefing

Another new feature powered by Cortana is calledBriefing. The service is simple and to the point: each day, you will receive a personalized briefing email that lists all your meetings, appointments, and other “actionable” items. Pending requests for response emails, documents, and commitments will all be provided, making these more than just a simple calendar recap.

There is also a “focus time” feature that highlights free time during your busy day and lets you easily schedule that in reminding you to take a break or have some personal time (it automatically silences Microsoft Teams notifications).

Cortana Briefing is currently rolling out in First Release for Microsoft 365 Enterprise users with Exchange Online mailboxes in English. You canread more about Briefing here.

AI in a data-centric world

What comes next for Cortana?

While there is no new news onCortana working with Amazon’s Alexa, besides the fact that the project is still going forward, Microsoft looks to have at least found a practical use for Cortana in a post-Windows Phone world.

Using Cortana to manage digital information — the kind prevalent on Windows 10, Azure, Microsoft Teams, and Microsoft Office — is needed in the modern workforce. Having an AI that can locate the right “Mike” in your company for an email, finding your relevant documents, and surfacing information proactively to manage your day is a major differentiator. These are actions that Google or Amazon cannot perform on Windows 10 (or Outlook), and never will.

Looking ahead, I’d like to see Cortana integrate into Microsoft Edge to manage my browsing history and collections. Trying to find that news article from days ago on that specific topic is better suited for AI instead of fallible human gray matter.

Another possible usage for Cortana I would find useful is tracking trends of products or topics I am interested in, proactively delivering updates.

With Cortana being a proper Windows 10 app now (it’s partially built on Microsoft’s UWP), it means it is no longer tied to bi-yearly OS updates. Instead, the Cortana team can now quickly iterate. And while the Android and iOS apps are being put to pasture, Shuman would instead put Cortana where millions of people are right now (Outlook, To Do, Office app, Microsoft Teams), versus trying to force them into yet-another-app.

The big challenge for Microsoft, and all other tech companies dabbling with AI, is can it actually make a digital assistant that feelssmart and useful? Time will tell, but this seems like the right start.

Back in black

Microsoft’s Surface Headphones are back, and they’re available in matte black and light gray. The Surface Headphones 2 also bring Bluetooth 5, up to 20 hours of battery life, aptX support, and more.

Microsoft’s super smart earbuds

Now at a lower price, the Surface Earbuds will undoubtedly turn some heads when you’re out wearing them, but you’ll be able to make use of gesture support on your PC, iPhone, or Android smartphone.

Daniel Rubino is the Editor-in-chief of Windows Central. He is also the head reviewer,podcast co-host, and analyst. He has been covering Microsoft since 2007, when this site was called WMExperts (and later Windows Phone Central). His interests include Windows, laptops, next-gen computing, and watches. He has been reviewing laptops since 2015 and is particularly fond of 2-in-1 convertibles, ARM processors, new form factors, and thin-and-light PCs. Before all this tech stuff, he worked on a Ph.D. in linguistics, watched people sleep (for medical purposes!), and ran the projectors at movie theaters because it was fun.