What is Cortana? A guide to Microsoft’s virtual assistant, and how you can use it to improve your productivity

Cortana on background
Microsoft’s Cortana assistant can handle a wide range of tasks on compatible devices and apps.

  • Cortana is Microsoft’s virtual assistant available for use across various devices and Microsoft 365’s suite of services and products.
  • To use Cortana, you must have the AI-powered assistant enabled through your Microsoft account and on relevant devices and services before saying the wake phrase “Hey Cortana,” followed by a prompt.
  • Cortana’s current iteration is geared towards productivity, focusing predominantly on saving you time and increasing your focus with tools like Briefing emails and Play My Emails.
  • Visit Insider’s Tech Reference library for more stories.

Microsoft’s Cortana is a cloud-based personal assistant that operates outside the realm of standard voice-enabled AI.

Cortana doesn’t just understand voice commands and carry out tasks but is integrated for use across Microsoft’s 365 suite of products and all Windows 10 operating systems, version 2004 and later.

If you or your team rely on Microsoft 365, here’s everything you need to know about how to harness Cortana to improve your productivity.

What is Cortana?

First launched in 2014, this virtual voice assistant’s name and concept were inspired by a 26th-century artificial intelligence character of the same name from the popular “Halo” video game series. Designed to integrate with the Windows Phone – and by 2015, Windows 10 PCs – Cortana’s capabilities included organizing and managing your daily meetings, reminders, and more alongside traditional web searches – all through typed text or voice prompts.

Everything you turned to Cortana for was then stored in a virtual “Notebook,” an approach to the virtual assistant that was based on the work of actual human assistants who spoke to Microsoft during Cortana’s development process, according to a 2014 Verge report.

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Cortana is integrated across Microsoft 365 products to keep your work and life synced.

From there, Cortana’s presence grew as Microsoft integrated it everywhere from Xbox and smart speakers to Apple and Android apps and third-party skills for Fitbit, Spotify, and more. But in the years since its launch, Microsoft users’ needs have changed, and the company’s vision for its digital assistant has evolved along with it.

What can Cortana do?

Nowadays, Cortana’s focus puts it in a different space than other voice-enabled AI assistants. Cortana primarily connects Microsoft 365 users to every element of their product suites and helps you track, organize, and manage your daily work.

Still available on Windows 10 and client applications like Outlook for iOS and Android, users can now go hands- and worry-free when it comes to managing their personal and professional work.

Included with any Microsoft 365 price plan, you can use Cortana with Windows 10 computers, the Edge browser, and Bing search engine; apps like Word, PowerPoint, and OneNote; email and calendar services Outlook and Exchange; as well as file services like OneDrive and Forms; and finally, social and meeting products like Teams and Yammer.

With Cortana enabled, using the assistant’s waking phrase followed by a command prompt can open apps, fetch the news and weather, add to your lists in Microsoft To-Do, schedule calendar event reminders, locate a file in OneDrive, join meetings, or navigate through presentations in Teams.

Voice assistant on phone

But Cortana can go one step further with personalized and interactive tools like Briefings and Play My Emails, both designed to ensure you’re at your most productive each day.

  • Briefing emails: Set up through Outlook, these briefs are sent within two hours of your workday to help you stay on top of the day ahead of you. Expect notes about outstanding commitments, requests, and follow-ups that you may have forgotten, documents relevant to the day’s meetings so you can review before you attend, and suggested focus times to help you get the most out of your unscheduled hours.
  • Play My Emails: If you need to go hands-free, this Outlook Cortana feature reads out your emails, so you don’t have to slow down to keep up. Best used with Bluetooth-enabled wireless or wired audio devices like headphones or your car audio, you can use simple voice commands for a touch-free inbox search and response experience.

How does Cortana work?

Regardless of the device, service, or program you’re using Cortana in, the Microsoft voice assistant helps users quickly get information using typed or spoken queries that connect you with other people, your work, and your plans. And with a stricter focus on assisting you with Microsoft products, Cortana can work more like an actual assistant than ever before.

While signed in to your Microsoft account and with the app or service you’re using open, just say “Cortana” or “Hey Cortana.” Cortana then responds to your requests and queries before completing relevant tasks. Simultaneously, it’s collecting certain data about you, such as your searches, calendar, contacts, and location, to help make future experiences with Cortana more personalized.

There are several ways you can prompt Cortana once enabled. These include clicking or tapping the microphone icon in Cortana-integrated products and services, executing the keyboard command “Shift + Windows Key + C,” or by saying “Hey Cortana,” followed by a vocal command. If you haven’t enabled Cortana on your PC, you’ll need to do so.

Cortana command prompts

Once Cortana is activated, you can use it for just about anything. Commands span basic requests about the weather, making calls and sending emails or messages, scheduling meetings, reminders, and alarms, as well as updating your device settings.

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Cortana keeps track of your past commands in one easy to read scrolling chat window.

But you can also use it for more complex things like math, translations, and definitions; food and travel recommendations; music and entertainment app control; personal health and fitness updates; technical support for connected devices; and fun or factual conversation.

Here are a few common prompts you can try:

  • “What’s the weather like?”
  • “Go to / Open [app name / website].”
  • “What’s [percentage] of [dollar amount]?”
  • “Where is my package?”
  • “Find photos from [date / time].”
  • “Find restaurants near me.”
  • “What is this song?”
  • “What was my step count yesterday?”
  • “Turn on/off Bluetooth.”
  • “Set an alarm for [date and time].”
  • “When is my [event name]?”
  • “Send email to (contact): (message).”
  • “Show me public transportation directions to [location / address].”
  • “Track flight [flight number].”
  • “Call (contact) at home/work.”
  • “Who’s my next meeting with?”
  • “How do I change default apps?”

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What is Outlook Web App? A guide to Microsoft’s web email service.

woman at home working desktop computer typing
In addition to the desktop and mobile apps, Microsoft Outlook can be accessed in a browser with Outlook on the web.

  • Outlook Web App, also known as Outlook on the web, allows you to access your Outlook email account from a web browser.
  • While Outlook on the web doesn’t include all the features found in the desktop Outlook app, it’s still convenient and useful.
  • You can set up out of office messages, see your tasks and calendar, change your theme, and more when using Outlook in a web browser.
  • Visit Insider’s Tech Reference library for more stories.

Outlook Web Access (OWA) is a browser-based way to access your Microsoft Outlook email. While it’s also been known as Outlook Web App, it’s now more commonly referred to as Outlook on the web.

OWA once applied exclusively to the online version of Outlook which came with Microsoft Exchange Server. These days, Outlook on the web is more commonly accessed from a Microsoft 365 or free Outlook.com account.

While the version of Outlook that runs on your desktop as an app for Windows or Mac still gives you the most flexibility, power, and features, you don’t need to use it – Microsoft makes it easy to open your Outlook inbox in a web browser instead. That means you can see your Outlook inbox from any computer.

How to open Outlook on the web

To open Outlook on the web, just open the URL that’s associated with your Outlook account. That should be the Microsoft 365 sign-in page or, if you have a free Outlook account, Outlook.com. Enter your email address and password and then select “Sign in.”

If you do happen to be using an Exchange Server rather than a Microsoft 365 account, you might need to ask your network administrator for the URL to the OWA website for your account.

How to use Outlook on the web

While Outlook on the web is a simplified version of Outlook, you’ll probably still recognize it as the email program you already know from the desktop. Here’s how to find your way around:

  • At the far left of the browser window is the folder list. It includes your Inbox, Sent items, and all the usual folders you have access to in Outlook.
  • To the right of the folder list is the message list. This displays all the messages in the currently selected folder, and the selected message appears in the Reading pane on the right.
  • You can also access additional features and settings from the toolbar at the top of the page and switch among Outlook’s modes (Inbox, Calendar, To Do, and Contacts) using the array of icons at the bottom left of the page, under the folder list.
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Outlook on the web displays your Outlook email in a web browser you can access from any computer.

How to view your Outlook calendar

To switch to the Outlook Calendar, just click the Calendar icon at the lower-left corner of the page. Here, you can customize the view. By default, you’ll see the Month view, but click “Month” at the top-right and choose the view you prefer from the drop-down menu.

You can add events and appointments to your calendar using the “New event” button at the top-left of the page. For more tips on how to get the most out of your calendar, read our article on the best tips and tricks to manage your Outlook Calendar on any device.

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The Calendar can be opened from the icons at the lower-left corner of the webpage.

How to manage your tasks and to dos

To switch to your tasks, click the “To Do” icon at the lower-left corner of the page. If your left-most pane is too narrow, you might not see the icon; instead, click the three dots and then choose “To Do” from the pop-up menu.

The To Do page has a task list pane on the left side of the page and the list of tasks on the right. To create a task, click the list in which you want the task to appear. Then, in the task pane on the right, click to the right of the plus sign and type your to do. You can mark a task by creating it in the “Important” list or by clicking the star after creating it.

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You can just click the text field beside the plus sign and start typing to create new tasks.

The best Outlook on the web settings

While you can get up and running with Outlook on the web in minutes, there’s a lot more power and customization hidden just under the surface. Here are some ways to get more out of Outlook on the web:

  • Filter your email. You can control what email is displayed and how it’s sorted. At the top right of the message pane click “Filter.” In the dropdown menu, you can choose which messages you want to see – such as all messages, only unread, messages directly addressed to you, flagged messages, and so on. To change the sorting method, at the bottom of the dropdown menu choose “Sort” and select how you’d like the messages to be organized.
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Outlook on the web gives you a variety of sorting options.

  • Configure the reading pane. You can set the Reading pane to appear on the right of the message pane (which is the default), underneath the message pane, or you can even disable it entirely. Click the Settings icon (shaped like a gear) at the top-right of the page and, in the Reading pane section at the bottom of the page, choose “Show on the right,” “Show on the bottom,” or “Hide.” If you choose to hide the pane, messages will appear in a new window and take over the Outlook webpage when you click on a message in the message list.
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The Reading pane can appear to the right or below the message list – or you can turn it off entirely.

  • Change your theme. Want a different theme for Outlook? Click the Settings icon (shaped like a gear) at the top right of the page and then choose a theme from the top of the Settings pane. There are more themes available than what you see here – click “View all” to see more.
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Use the Settings icon to change the visual theme of Outlook on the web.

  • Turn on dark mode. Dark mode is a popular feature that some people find easier on the eyes, especially in the evening hours. Click the Settings icon (shaped like a gear) at the top right of the page and then and then turn on Dark mode by swiping the button to the right.
  • Turn on desktop notifications. If you’d like to see a pop-up notification about new messages even when your browser is not the focus of your desktop, you can turn on desktop notifications. Click the Settings icon (shaped like a gear) at the top right of the page and then turn on Desktop notifications by swiping the button to the right. In most cases, you’ll also need to enable your browser to show notifications – look for a pop-up from your browser to enable these notifications. If you’re using Chrome, for example, click “Allow.” In Firefox, click “Allow Notifications.”
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If you turn on notifications, be sure to enable notifications in the browser as well.

  • Customize display settings with display density. You can vary how many messages appear in the message list at once – you can pack them in more tightly or space them out, making them easier to browse. Click the Settings icon (shaped like a gear) at the top right of the page and find the Display density section. Choose “Full,” “Medium,” or “Compact.” Full is the most relaxed view and each message includes a small icon representing the sender. Medium removes the icon, which shrinks the size of each message slightly. Compact tightens up the spacing and puts the most messages on the page at once.
  • View and group your conversations. You might be familiar with Outlook’s Conversation view from the desktop version of the email app. Conversation view groups related emails together, making it easier to follow a conversation thread. You can control this setting in Outlook on the web as well. Click the Settings icon (shaped like a gear) at the top right of the page and find the Conversation view section. You can arrange your email so the newest replies in a conversation appear on top, appear on the bottom, or you can turn off conversation view entirely. If you do that, every message appears independently in the message pane, regardless of its relationship to other messages.
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You have several options for configuring how to group and view messages in Outlook on the web.

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The 6 best tips and tricks to manage your Outlook Calendar on any device

business professionals working together at desktop laptop in office
Your Outlook Calendar can be customized in many ways to suit your professional and personal needs.

  • You can use these tips and tricks to get the most out of your Outlook Calendar on a variety of devices.
  • The Outlook Calendar can be accessed in a desktop app, on the web, or in a mobile app, though only the Outlook desktop app includes all of the service’s features.
  • You can create a free account to use the Outlook Calendar on the web, but a subscription to Microsoft 365 gives you the most features.
  • Visit Insider’s Tech Reference library for more stories.

Microsoft has offered a full-featured calendar as a part of its Microsoft 365 suite of productivity apps for decades. But rather than being a stand-alone program like other apps, Office’s calendar is so well integrated with the Outlook email app that they are literally the same program; the only way to see your digital calendar is via Outlook.

There are a lot of lesser-known features hidden in the app, and unless you’re already an Outlook power user, you’ll find that there are a lot of ways to get more out of your Outlook Calendar.

How to get an Outlook Calendar with or without Microsoft 365

Microsoft’s digital calendar is only available as a part of Outlook. You can get Outlook three ways: with a Microsoft 365 subscription on desktop, for free on the web, or as a mobile app for iPhone and Android.

The most full-featured version of the calendar is on the desktop with a Microsoft 365 subscription, such as Microsoft 365 Family ($100 per year) or Microsoft 365 Personal ($70 per year). In addition to giving you access to the full suite of Office apps, these subscriptions also include OneDrive storage.

Without a subscription, you can still access the Outlook Calendar on the web or via the mobile app, though with fewer features and capabilities.

Outlook Calendar tips and tricks

There are countless ways to personalize your Outlook Calendar to get the most out of the program. Here are some of the most useful tips and tricks.

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Okta drops after company gives weak guidance and announces $6.5 billion Auth0 acquisition

Okta Auth0 deal
Okta cofounders Frederic Kerrest and CEO Todd McKinnon (top L to R) on a video call signing the agreement to acquire Auth0 for $6.5 billion with its cofounders CEO Eugenio Pace and Matias Woloski (bottom L to R)

  • Okta fell by nearly 10% Thursday as the ID-authentication software company’s outlook missed Wall Street’s view. 
  • The company expects a first-quarter adjusted loss of $0.20 to $0.21 a share compared with the consensus of a loss of $0.07. 
  • Okta plans to buy rival Auth0 in a transaction valued at $6.5 billion. 
  • Visit the Business section of Insider for more stories.

Okta shares dropped nearly 10% Thursday following a quarterly outlook that missed Wall Street’s estimate while the identity-authentication software maker said it plans to buy rival Auth0 in a $6.5 billion stock deal.

The company late Wednesday projected a first-quarter adjusted loss of $0.20 to $0.21 per share, which was wider than the consensus estimate of a per-share loss of $0.07. It also expects year-over-year growth in total revenue to $237 million to $239 million compared with Wall Street’s view of $237 million.

Shares of Okta lost as much as 9.6% when it hit an intraday low of $218. The stock later pared the decline to 4.5%. Over the past 12 months, the shares have advanced about 79%.

The company’s projection came within its fourth-quarter financial report and alongside a separate announcement about planning to buy Auth0. Okta said its guidance does not include any potential impact from the proposed Auth0 deal.

Okta said the pending deal will stoke growth in the $55 billion identity market. Auth0 will run as an independent business unit inside of Okta and both of its platforms will be supported and integrated over time.

The transaction “will accelerate our innovation, opening up new ways for our customers to leverage identity to meet their business needs,” said Todd McKinnon, Okta’s CEO and co-founder, in the statement.

For the fourth quarter, the company posted adjusted earnings of $0.06 a share, swinging from a loss of $0.01 a year ago. Revenue of $234.7 million increased from $167.3 million in the same period a year ago.

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‘Dr. Doom’ economist Nouriel Roubini warns Biden’s presidency will suffer civil unrest and cyberattacks by Russia and China during his term

Nouriel Roubini
  • Economist Nouriel Roubini expects Joe Biden’s presidency to face civil unrest and cyberattacks.
  • Russia and China will launch cyberattacks against the US and spread false information, he said.
  • He’s worried Donald Trump could execute military action in Iran, making things difficult for Biden.
  • Visit Business Insider’s homepage for more stories.

Joe Biden’s presidency can expect to go through civil unrest and cyberattacks, “Dr. Doom” economist Nouriel Roubini told German magazine Der Spiegel on Friday.

Biden’s term will face more armed uprisings, especially from white nationalists, mainly to provoke the left-wing, the economist said in an interview with Tim Bartz.

According to Roubini, who is famous for his pessimism, Russia and China will launch cyberattacks against the US and circulate false information. 

“That will shape the next four years,” he said, according to a transcript translated from German. 

But in the short-term, the American economist is more worried that President Trump could strike an attack on Iran’s key nuclear site in Natanz – the only uranium enrichment plant in the country that’s allowed to operate under the nuclear deal.

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Trump’s administration has engaged in aggressive foreign policy against Iran throughout his term and imposed a number of sanctions on a number of Iranian targets.

Biden, who will succeed Trump on Wednesday, has declared to return to the 2015 nuclear pact as long as Iran resumes strict compliance with it, according to Reuters.  

Trump could execute military action against Iran’s key nuclear site to present himself as powerful to his supporters and make life more difficult for Biden, according to Roubini.

The economist also called for tighter regulation on Big Tech platforms, such as Facebook and Twitter, because of their power. Since antitrust rules are devised for traditional monopolies, separate rules should govern social-media companies that have distinct structures, he said.

Read More: GOLDMAN SACHS: Buy these 25 stocks best-positioned to juice profits in 2021 as stimulus and vaccine progress spur economic growth

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