Microsoft Cortana reading email aloud on an iPhone is surprisingly useful, to a point – GeekWire

Microsoft’s new “Play My Emails” feature is available first on Outlook for iPhone. (Microsoft Photo)

Grab your headphones, press play, and groove to the sound of your email inbox.

It might sound a little weird, but based on my experience so far, Microsoft’s new “Play My Emails” feature for the Outlook app on Apple’s iPhone is a surprisingly useful and well-executed tool for keeping on top of your email, which despite the rise of workplace chat is still a critical communication channel in many jobs.

The feature, announced last week, uses Microsoft’s Cortana voice assistant to provide updates on appointments and events, summarize how many important messages have come in since last check, and say how long it will take to get through them, before reading them. With voice commands, users can flag messages for follow-up; archive, delete or skip messages; and dictate and send short replies.

A simplified on-screen overlay appears in the Outlook app while navigating emails via voice command. (GeekWire Screenshot)

It works especially smoothly with Apple AirPods and Microsoft Surface Headphones, pausing playback when you remove them, for example. It also works normally with other Bluetooth-enabled wireless audio devices, including in-car infotainment systems, integrating with basic media controls in the vehicle.

The voice interface is easy to navigate, and at its best, the experience feels almost like you’ve got a human assistant helping you manage your calendar and email.

Yes, the prospect of receiving email in the ears will make heads spin in a world already suffering from information overload. (I can hear people saying, “Can’t we all just chill out and listen to music?”) The initial version also lacks some key capabilities, such as the ability to forward or categorize/label messages. And because of the natural limitations of voice controls, this will not fully replace the normal way of using email on computers and smartphones anytime soon.

But in the situations where “Play My Emails” is useful, it’s very useful.

For example, you can catch up on email while driving back to the office after a long meeting, or make sure you don’t miss a late-afternoon message on the walk to the bus stop after cutting out early. Or you can catch up on messages from overnight while you make your morning coffee.

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With apologies to your favorite podcast, just imagine how much email you can get through in the time it takes to do the dishes or fold the laundry.

Using “Play My Emails” with the Outlook app on iOS. (Microsoft Photo)

Full disclosure: I am a text-to-speech nerd, and I think we’re just at the beginning of the practical applications of these types of approaches. For example, one of my favorite things is saving long articles from the web to the Pocket app, then using its automated voice feature to listen to saved stories on the go. I also frequently edit stories while listening to them with a text-to-speech browser plugin.

This is one reason why I was so interested in testing the “Play My Emails” feature. So I may be a bit of an outlier.

Even so, I can see this helping a lot of people.

How it works: The “Play” in “Play My Emails” is a bit of a misnomer, and I think it sells the feature short. It’s more like Cortana is intelligently narrating your calendar and inbox, a.k.a. your life. (Kidding, sorta.)

“I’ve got two emails for you right now,” Cortana told me when I woke up this morning. “This will take a couple of minutes.”

This was much better than the first time I tried, toward the end of a busy week, when Cortana said I had 61 new email messages that would take 40 minutes to get through. I processed part of the backlog with Cortana’s help before finishing the process on my computer.

When reading messages, Cortana follows this general pattern, “[In this time frame], [name of person] [sent/replied/forwarded] an email about [subject] to you and [number or name of other recipients.]”

Cortana then provides a sense for how long the message is before reading it. “It’s a long one,” is the phrase used before reading a message will take more than 30 seconds. When it will take more than a minute, she warns, “It’s a really long one.” (Messages from my colleague and GeekWire co-founder John Cook tend to come with this warning.)

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When Cortana is reading the text of the email, a simplified overlay on the screen resembles a music app, with play/pause, archive and flag buttons underneath the subject line and a photo or initials of the sender, providing an alternative to voice commands. You can swipe back and forth on the screen to navigate between messages if you’re holding your phone, or if not, you can give voice commands to go back or forward in the queue of messages.

Quality of experience: The feature was used and tested for months by Microsoft employees before its public debut, and it shows.

Cortana hears accurately, responds reliably, and does a solid job of taking dictation. Between that and the increasingly human-like intonation and conversational quality of Cortana’s virtual voice, there are moments when the experience truly feels like artificial intelligence: technology effectively replacing the capabilities of a human.

(I also tried the new male voice option for Cortana, available with this feature, but it sounds much more computerized and less natural, so I switched back to the normal Cortana voice.)

The synchronization between the feature on the Outlook app and my standard desktop inbox is seamless, updating within seconds. I was able to use the feature with both my Microsoft account and Google email accounts in the Outlook app (Gmail and Google Apps), and the sync to the first-party Gmail/Google webmail and smartphone apps was also smooth with these non-Microsoft email accounts.

Limitations: The inability to forward or label/categorize messages using voice commands seem like glaring omissions that should be addressed later.

That said, when it comes to the limitations, Cortana is also very self-aware. When a message contains a bunch of images, for example, Cortana says the email has a lot of visual content, “so it’s better read on a screen.” After reading the text of some messages, Cortana will tell you that there are embedded links, or more to the email that requires a screen.

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You can launch the feature from the Outlook app inbox or set it up to launch via voice command from anywhere in the phone.

One result of Microsoft not having its own smartphone platform is that you have to say, “Hey Siri” for this initial invocation, telling Apple’s voice assistant to “read my email,” or another custom phrase. Once you get past this awkward moment, however, Cortana does the actual work. You can invoke Microsoft’s assistant via voice or the microphone icon to give voice commands. Cortana also pauses at key moments and beeps to signal that she’s ready for a voice command.

The feature is available only on iPhone and in the U.S. for now. “Play My Emails” is not available internationally or for Outlook on Android yet. This is frustrating. Wasn’t the idea for Samsung to offer the premier Windows and Microsoft integration? I’m biased on this point, after switching to a Galaxy Note 10 Plus to try out the Windows integration. But it would be great if Microsoft would pick a lane, or better yet, release new features simultaneously on both platforms.

Fortunately, I figured this type of thing might happen, so I kept my iPhone, too.

Bottom line: Microsoft says “Play My Emails” is the first Cortana feature to be released as “an integral part of the Office 365 core experience,” and it’s a good start.

This is part of a broader effort by Microsoft to focus Cortana on productivity across a variety of devices, after giving up on the notion of competing head-to-head with the likes of Siri and Alexa as an all-purpose voice assistant.

The new feature started rolling out earlier this week in the Outlook app for iPhone, available in the iOS App Store, although Microsoft says it may take several weeks to reach all U.S. users.


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