Start a conversation with your personal productivity assistant in Outlook with Cortana
Published Feb 01 2021 12:14 PM 49.4K Views

You carry your mobile device with you to every room of your house, to friends’ places, on walks and to and from the office or at home. Your mobile device has truly become your daily companion, at your fingertips to help you stay connected to people and things that matter. Imagine if that companion could provide extra help during your day. To this end, Microsoft will soon introduce new conversational AI experiences with Cortana, your Microsoft 365 personal productivity assistant, in Outlook for iOS to help reduce the effort required to get things done quickly and easily on an iPhone or iPad.


With your mobile device at your side virtually all the time, using your voice offers a fast and easy way to manage your time and inbox.  We are exploring ways Cortana can help to schedule meetings, compose email messages, and find files, emails, and people that are relevant to you using the power of human voice in Outlook. Using natural language, speech recognition, machine learning, and linguistics based on Microsoft AI technology, Cortana will get to know you and your voice to help you stay organized, connected to people and things that are important to you, and stay in control of your day.




How and when can I get Cortana’s assistance in Outlook?

We will start the roll out conversational AI in Outlook for iOS in the coming weeks. However it will take a month or so after that to reach all the eligible customers. You’ll know it’s available when your Outlook app updates, and you see new event and message buttons on your Inbox and Calendar screens. When pressed and expanded, an Ask Cortana microphone icon will be available as well as other common Outlook tasks. We will continue to add more and more capabilities over time. As a personal productivity assistant that is a natural part of Microsoft 365, Cortana processes data safely and securely to meet your needs.

Long press the new message button in Outlook for iOSLong press the new message button in Outlook for iOS



Initially, this new conversational AI capability with Cortana will be available in English for customers in the United States using Outlook for iOS with a Microsoft 365 work account.  


Managing your time in Outlook with help from Cortana


Managing your time and your commitments effectively can be challenging on a mobile phone. By delivering assistive experiences, Cortana can help schedule new events and customize the event details on the screen with language that you use every day instead of tapping or typing. Cortana can help you stay connected to the people and events that are relevant to you with insights from the Microsoft Graph so it’s easier to stay on top of important commitments. With time and location suggestions, planning your day in Outlook can help save you time and effort when you ask Cortana for assistance.


For example, if you would like to schedule a meeting next week with 3 colleagues, it may take you more than 15 screen taps to set that up although Outlook can proactively suggest people and locations and can enable you to have Teams Meeting on by default. This new capability allows you to simply ask Cortana in Outlook to:

Schedule a Teams Meeting on Tuesday next week with Megan and Adele at 2 PM to discuss the launch.”


Conversational AI allows you to have a conversation with your personal productivity assistant. You will be able to ask Cortana to change meeting recipients, dates, times and eventually the location based on your preferences for your meeting or focus time, all with your voice.


For example, when creating a new event using your voice, you can say:

“Schedule a meeting with Megan and Adele tomorrow at 2PM to discuss the Budget …

Change it to 3PM …

Change the title to 2021 Planning and add Nestor.”


Or if you are a participant and not the organizer or host of an event, you can ask Cortana about details of the event. For example:

“Has anyone accepted this meeting?”


Or do something with it:

“Forward this event to my manager.”


We will also add a new microphone button at the top of your events’ details page on your calendar.  You will be able to ask Cortana to:

“Add Lee to this, make it a Teams meeting, make it a private appointment …

Move this meeting to 4PM.”


And building on Microsoft Search capabilities that are available in Outlook mobile today, you will be able to ask Cortana to find specific events. 



You can use your voice to search for events with specific people in your organization over a specific timeframe making it a more natural and efficient experience.


Continue the conversation with email


You will also be able to use natural language voice commands in your Inbox and email messages. We are starting by delivering the assistive experience with Cortana to help you compose quick messages, forward emails to your contacts or people in your organization and reply to the sender or all the recipients of the message or conversation thread.


The new message button on your Focused Inbox will give you the ability to ask Cortana to start a short message. For example, you can press the new message button and tap the mic icon to ask Cortana to:

“Send an email to Adele about 2021 planning” – a new message will start to be created with your colleague as a recipient and the subject completed as “2021 planning”. Then you can type the rest of your message. 


In the coming months, we will make it easier to compose full, longer email messages by adding Dictate to Outlook for iOS. This way, you will be able to continue composing messages using your voice and natural language the same way you can today in Office mobile with Word, and like the Dictate option in many Microsoft 365 Windows and Mac apps with this voice-enabled capability.


In addition, we are introducing another new way to quickly manage your messages as you read them. With a new microphone at the top of the message or conversation you have opened in Outlook; you will be able to do things such as:  

“Forward this to my manager” – Outlook will set up the message with your manager’s email address in the To: list where you can add more recipients and add a typed a comment.


“Reply to this” or “Reply to all” or “Reply and add Alex to this” – similarly Outlook will set up the message with the appropriate recipients so you can quickly add additional text and simply send your response.


This new mic in your messages will also enable you to start Play My Emails in Outlook for iOS so you can continue a hands-free experience and choose to listen to Cortana read out your new messages in your inbox and changes to your day.  


More options to play emails in Outlook


We are excited about our investments in assistive experiences as we continue to build upon Play My Emails capabilities in Outlook with Cortana. We are adding additional options to personalize your experience in ways that help you get time back in your day, stay organized, and get things done quicker.


For example, by the end of February you will be able to open an email message in Outlook and if it is one you would like to listen to rather than read, you can choose to play the conversation from an option within the ellipses.

Start the Play My Emails experience from an open message in OutlookStart the Play My Emails experience from an open message in Outlook


With Play My Emails running, at any time you can interrupt the readout by touching the mic on the screen or saying, “Hey Cortana”. Soon you will be able to ask Cortana to play messages from specific people, such as your manager or someone else in your organization and over a range of time, such as “last week” or “in January”. Or you can customize Play My Emails in Outlook settings to only listen to updates from your Favorite People or Favorite Folders so it’s easier to stay on top of what’s important to you.

Personalize your Play My Emails experience in OutlookPersonalize your Play My Emails experience in Outlook


We have also learned that users often tap through Outlook to start Play My Emails as soon as they connect their smartphone to their car audio system. We have added an option to automatically do that so you can get going to your destination straight away. This is not on by default, but you can turn it on in Outlook settings. 

Autoplay Play My Emails when connected to your car audioAutoplay Play My Emails when connected to your car audio

For added convenience, we also added the ability for you to set a Daily Reminder to start Play My Emails on a scheduled basis. This way you can Play My Emails on your preferred day at your preferred hour, so you stay on top of what’s new when and where you choose.


It is our pleasure to bring new, helpful ways to manage your time and organize the important things in your daily life. We are excited to embark on this journey with you to explore what conversational AI can enable you to do more quickly and with less effort. As your mobility and connectivity needs evolve so too will the capabilities we bring through intelligent technology in Outlook with Cortana.


Please try these new capabilities once they become available to you and let us know what you think by adding a message below or at To watch an exciting video learn more about this and other new mobile productivity features rolling out across our Microsoft 365 mobile apps, visit



Frequently asked questions 


What does conversational AI mean?

With Microsoft AI we strive to help people to be more productive in many ways including using voice interaction in a natural, conversational way. We believe to be truly helpful and reduce the effort to get things done requires the capability to extend across multiple domains (e.g. mail and calendar) and be able to take multiple commands in sequence (multi turn) while being contextually aware of what is happening in the application in a similar way that a conversation evolves. 


This experience relies on enterprise-grade services including Cortana in Microsoft 365, the Microsoft Graph, the algorithms and the intelligent technology developed by the team that joined Microsoft from Semantic Machines.  


How is the voice data handled?

Please refer to the section about Conversational AI in Outlook with Cortana here:


Are these updates coming to Outlook for Android?

Yes, we are working on providing a similar experience in Outlook for Android while we learn from this initial experience from customers using Outlook for iOS.  We anticipate it will be a few months before we are ready to expand to the Android platform.


Can I use my personal email account such as

The initial release of conversational AI in Outlook with Cortana will not support or Gmail accounts.   




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