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Microsoft Cortana

Cortana is Microsoft’s productivity assistant that offers AI-powered experiences to save time and focus attention on what matters most. With Cortana, conduct online searches, set appointments, draft emails and create calendar events. 

Note: Cortana was once integrated with the Windows 10 search box but was separated after May 10, 2019.


How do I start using Cortana?

  • To get started, click the Cortana icon on the taskbar. Sign in using your Penn Carey Law Email. If you’re not sure what to type, try asking, “What can you do?”


Here are some things Cortana can do for you:  Manage your calendar and keep your schedule up to d...

Here are some things Cortana can do for you:

  • Manage your calendar and keep your schedule up to date.
  • Join a meeting Microsoft Teams or find our who your next meeting is with
  • Create and manage lists
  • Set reminders and alarms
  • Find facts, definitions, and info
  • Open apps on your computer

Cortana voice assistance in Teams

Stay connected with your team even when you have your hands full, Cortana is available on Teams mobile app on IOS and Android. 

Play my emails in Outlook

Cortana can help you stay on top of what’s new in your inbox with Play My Emails in Outlook. This is a new feature available ONLY to iOS and Android devices. The new user experience is optimized for people on the move and works best when you’re connected to an audio device, such as Bluetooth-enabled wireless or wired headphones, or your car audio. Now interact with your inbox while your phone is in your pocket. 

Note: By default Play My Emails is disabled. Open Outlook, click your profile picture and click the ▶ icon to enable. 

Learn more:


  • How do I start using “Play My Emails?”
    If you’re connected to an audio device (wired or Bluetooth), select the Play icon in the notification that appears at the bottom of the screen. Otherwise, open Outlook, swipe right from the left side of the screen to open the side menu, then select the Play icon.
  • Which emails will Cortana read?
    First, Cortana will read out any changes to your schedule that will occur over the next 24 hours. After that, it will read out the 30 most recent unread emails that you’ve received in the past 24 hours. For conversations within a single email thread, the oldest message will be read first. If you’ve enabled Focused Inbox, only emails in the Focused Inbox will be read.
  • Can I reply to email messages?
    Yes. By default, your response will be sent to all recipients of the email thread. If you only want to respond to the original sender, reply “No” when Cortana asks if you’re ready to send your response. Cortana will then offer to reply only to the original sender. Cortana does not incorporate dictated punctuation into spoken messages.

Microsoft Todo

As part of Cortana’s recent change, any and all lists or reminders created through Cortana will appear in the  Microsoft To Do app.  

Cortana Daily Briefing

Cortana Daily Briefing email helps you stay in control of your calendar and be intentional about your day. Within a few hours of the start of your workday, you’ll get an email about any relevant items to help you better prepare for the day ahead, including:

Prepare for meetings by showing you related tasks or documents related to today’s meetings.

Follow up on tasks that remind you of pending tasks from email threads.

Make the most of focus time by scheduling time on your calendar that silences notifications for uninterrupted, independent work.

How does it work?

Daily Briefing emails are personal and private and are only sent to you directly in your mailbox, which cannot be accessed by anybody else in your organization, including ITS. Briefing email data uses Exchange Online email and calendar data and processes and stores any insights or actions inside your Exchange Online mailbox, so data security is built-in and enforced by Exchange.

  • Briefing Emails do not include any new, personally identifiable information about anybody else in your organization.
  • Your Briefing emails are based on information that you already have access to but can’t quickly aggregate without help. For example, if you want to determine what commitments you made to others, you could manually review each email in your mailbox. The Briefing email helps you avoid this time-consuming process.
  • The Briefing email looks for actionable tasks in Outlook and includes the top results in the email. If these tasks are related to any upcoming meetings, they’ll be listed in context with the meeting. Meetings will also have links to any attached or potentially related documents.

What emails? I’m not receiving anything from Cortana?

If you haven’t received an email, then daily briefings may be disabled for your account. Contact ITS to verify your subscription status. In addition to the subscription status, sometimes, Cortana does not have enough data(Outlook data) to provide you with a daily briefing email. The more you work in Microsoft Office365, Teams, Outlook, and SharePoint, the better your daily briefs will be.

Can I opt-out of the Daily Briefing email?

To opt-out or verify your subscription, visit or contact PennLaw ITS at

Learn more

LinkedIn Learning 

Visit LinkedIn Learning to learn everything there is to know about Cortana and other Windows 10 features. 

  1. Sign in here: with your PennKey
  2. After signing in, click on any of the below course videos.

More Resources

FAQ - Cortana Daily Email Briefing 

What’s new with Cortana?

What is Cortana?

What can you do with the Briefing email from Cortana?

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