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Five Things You Didn't Know About Cortana, Microsoft’s Virtual Assistant

She's funnier than Siri, for one thing.

Vjeran Pavic

Update, Jan. 22, 2015: Earlier this week, Microsoft unveiled its new Windows 10 operating system for desktops, due out later this year, and demonstrated how its mobile virtual assistant, called Cortana, will migrate to the desktop. While specifics about Cortana’s functionality in the new OS are unknown, Microsoft revealed that Cortana will be able to set reminders, customize Windows settings, run Web searches and find locally stored content.

Below is the original review, published Sept. 22, 2014, detailing some features of Cortana on Windows Phone.

We’ve put Apple’s Siri through the wringer, and have given Google Now an all-access pass to our data, all the while documenting our experiences to offer you the best tips and tricks out there for intelligent assistant apps. Now it’s Cortana’s turn.

Cortana is Microsoft’s virtual assistant for smartphones, specifically phones running Windows 8.1. She’s named after a fictional AI character in Microsoft’s hugely popular Halo videogame series.

In some ways, Cortana is a kind of combination of Siri and Google Now (with, arguably, more personality). She can perform task-based functions: She shows you your daily schedule, sets alarms and sends reminders. But Cortana also provides search-based information, courtesy of Bing.

I’m going to go out on a limb here and say that the majority of you have never used Cortana, given that Windows Phone accounts for just 2.5 percent of mobile operating systems worldwide. And even if you are on Windows Phone, you might still be waiting for an OS update that gives you access to Cortana. Microsoft says that roughly 90 percent of Windows phone users have access to Cortana right now.

Cortana is not perfect, which I’ll get into in a bit. In some instances, the app requires a specificity of questions that the other virtual assistants don’t.

But if you are a Windows phone user — or you’re seriously considering switching to a Windows phone — here’s what you need to know.

Cortana wants to get intimate right away

Like actual assistants, most virtual mobile assistants are supposed to get to know you over time. But Cortana dives right in.

When you first activate Cortana, she’ll ask you a series of personal questions, like, “What are a couple of the most enjoyable parts of your everyday evening? When you think about food, what’s the most important to you these days? What do you look for when you want to catch up on the world?” As explained in the app, this is so she can get “smarter” about your preferences.

After five days of testing Cortana, saying something like, “Cortana, show me the news” still resulted in a mixed bag. In general, the more specific I was (“Cortana, show me health news”), the better the results were.

One feature I do like within the whole Windows Phone experience is the “live tile” aspect. This lets me see a cycle of news headlines within the Cortana tile on my home screen, making it more like an active widget than an obfuscated app.

He’ll keep calling me, he’ll keep calling me …

This is my thought process when I entertain the idea of being smartphone-free for a day: Wow, wouldn’t it be nice to turn off my smartphone this afternoon and just enjoy the day? Well, except if someone calls with a family emergency. Or Walt calls. Or Kara. Or that source I’ve been trying to get in touch with for three days. Or …

Fortunately, Cortana has features similar to the Do Not Disturb setting in iOS. They’re called Quiet Hours and Inner Circle, and they let you set the terms around whom you want to communicate with and when. You can turn on Quiet Hours — which means your calls will be sent to voicemail, and you won’t get text alerts — at any time, or you can preset your Quiet Hours.

Then you can add a list of names to your Inner Circle to allow just those contacts to “break through” your Quiet Hours.

Cortana: Remind me to ask Walt for a raise

Siri, Google Now and Cortana all help you set reminders on your smartphone. Google Now and Siri even allow these to be location-based. (Google: “Remind me to pick up coffee next time I’m near a Safeway”; Siri: “Remind me to call Hermione when I leave work.”) But Cortana adds another layer of context: You can set a reminder to say or do something the next time you’re communicating with someone.

For example, by going into Cortana –> Settings –> Remind Me, I was able to add a reminder to ask my mom about her new job the next time she called, texted or emailed me.

Some of you might think, If you’re a decent human being, you wouldn’t need a reminder to ask your mom how she’s doing. Yes, of course! I’m with you. But we could all use reminders sometimes. It’s helpful for work-related stuff, too.

Cortana as social media marketing assistant?

Unlike other virtual assistant apps, Cortana works deeply with a bunch of other third-party (read: non-Microsoft) apps out there, like Foursquare, Twitter, Hulu Plus and more.

So, you can pull up Cortana on your phone, say “Foursquare, check me in,” and Cortana will immediately open Foursquare with a list of local places to check into. When I said, “Facebook, what’s up with Walt Mossberg?” Cortana immediately brought me to my boss’s Facebook page. And when I said, “Twitter, new tweet,” Cortana opened up the Twitter app and listened for my tweet dictation.

You know it’s okay to still want privacy … right?

It can be a little unnerving to give an intelligent assistant app so much access to your personal information. As with a real-life assistant, you’d want to be able to kick them out of your office, or to revoke access to your calendar whenever you want. (I assume. I’ve never had an assistant. But, you know.)

As my Re/code colleague Bonnie Cha wrote in her review of Windows 8.1, Cortana gives you a little more control over your shared data in something called Cortana’s “notebook.” This is located within the Settings tab in the upper-right-hand corner of the screen, and this is where you can, with a series of taps, delete any preferences, connected apps or access to data gleaned from emails on your phone.

It’s worth noting that Apple recently put up a Web page detailing its privacy policies around iOS 8, and that included some info around Siri. Among other things, it says that when a user turns Siri and dictation off, Apple will delete your user data, as well as recent voice-input data.

But like I’ve said before, these virtual assistant apps generally require you to hand over a lot of digital data in order for them work effectively.

Bonus Tip: Cortana, who’s your daddy?

Cortana’s answer: Technically, Bill Gates. She also has some fun answers to prompts like “Tell me a joke,” “Do an impression,” and “Do you know Clippy?” This is one of the reasons that I said earlier that Cortana shows a little more spunk than the other virtual assistants. (Siri shows you Web results for “how to do an impression.” She wouldn’t last a season on “Saturday Night Live.”)

In conclusion …

Cortana is clearly not perfect. In my experience, she was great at tasks — setting alarms, taking me through my calendar — but not as great at answering some everyday questions. My Re/code colleagues have observed this, too.

In side-by-side tests, I asked Cortana and Siri things like, “How are the San Francisco Giants doing?” and “Take me to Recode-dot-net.” Siri performed well: She dictated that the Giants are in fourth place in the National League, with a record of 84-69, and her top Web result was our site, Cortana’s answer about the Giants was an ad for San Francisco Giants Gear (yuck), and then she simply listed the most recent game results. And she couldn’t figure out my verbal request for “Recode-dot-net.”

But if you’re a Windows Phone 8.1 user, hopefully this guide will help you get the most out of Cortana.

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