Scheduler, a new Microsoft 365 service, makes scheduling meetings easier and faster
Published Jun 08 2021 08:00 AM 55.7K Views

It’s not just you: weekly meetings have increased by 148% and the time that employees spend trying to schedule meetings both inside and outside of their organization is climbing.  With the average time to schedule a meeting taking 6 to 29 minutes, Scheduler aims to give you back time to focus on the important things by making it easier, faster, and being available 24/7 to schedule meetings for you, and it’s available starting today.


Let’s dig into what makes Scheduler work.


Scheduler understands natural language

Scheduler understands what you write, so you can word your requests to Cortana just as you would when asking any person for assistance scheduling a meeting in an email. As simple as “Cortana, please find a time to meet next week,” to something more detailed like “Cortana, please find us 45 minutes in the last week of the month in the morning for Pacific time and make it a Teams meeting.” As Scheduler learns, you may receive responses from Cortana asking you to clarify certain asks or to provide more details in order to complete your request.


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Ask Cortana in your own words to schedule a meeting


How Scheduler and Cortana work together

Although Scheduler and Cortana complement each other, they are separate – and different – parts of the user’s experience. Scheduler is a backend service that provides the scheduling intelligence, workflow, and can be enabled by the Microsoft 365 administrator. Cortana, the productivity assistant in Microsoft 365, acts through a custom mailbox* that is configured by the administrator. Cortana also provides the frontend assistant that users interact with through email conversations to schedule a meeting.


Microsoft 365 administrators can create a custom mailbox for Scheduler and through a new PowerShell commandlet configure it to process meeting requests in natural language from users in their organization, including looking up attendee availability, negotiating times over email, sending calendar invites, and even rescheduling or canceling a meeting if needed.


Scheduler is enabled independently from other Cortana services, such as Cortana for Windows 10 and the Briefing email from Cortana. If an organization already has Cortana enabled, they also would need to purchase and enable Scheduler, the other Cortana experiences do not have to be enabled for someone in the organization to use Scheduler.


Delegate scheduling across multiple scenarios

Once the assistant’s mailbox has been created, users with a Scheduler license can ask Cortana to schedule their meetings by sending Cortana an email. Here are the 3 most common scenarios:

  • Easily schedule a meeting with people inside your organization, with one email – With Scheduler, Cortana has access to the same information you do you when scheduling meetings, including you and your colleague’s Outlook free/busy availability without having access to any further details. This means Cortana knows when you and your colleagues are free or busy and can find the times that work for everyone without you having to peruse everyone’s availability.
  • Skip the back-and-forth emails when scheduling a meeting with people outside your organization – Scheduler provides Cortana access only to your organization’s free/busy availability. To negotiate a meeting time with people outside of your organization, Cortana will suggest a few times when you are available to the other attendees over email. The attendees outside of your organization can accept the times Cortana proposed or suggest new times over email. Once consensus has been reached, Cortana will send meeting invites to everyone.
  • Let Cortana manage more complex scenarios when meeting with people inside and outside of your organization – Because Cortana has access to some of the attendees free/busy availability, Cortana will find times that work for that subset of attendees and then propose those times to the people outside of the organization. Once consensus has been reached, Cortana will send meeting invites to everyone.

Cortana will find the way with human assistance when needed

Part of the reason why Cortana will always find a way to schedule your meeting is because when the technology can’t complete your request, it relies on human assistance to figure out any incoherence or to ask the organizer for specific questions that clarify the request. Most of the scheduling requests are completed automatically by Cortana but there could be instances where human assistance is needed. The human assistance that supports Cortana is part of Microsoft’s Supplier Privacy & Assurance Standards and are bounded by Microsoft's Privacy statement. If a request needs human assistance, they will have access to the email conversation from the point in which Cortana was added to the conversation, Microsoft Graph data, names, and emails of the people involved in the conversation but they will not have access to links nor attachments. Additionally, Scheduler will not process encrypted messages sent to the Cortana mailbox.


You control your data

The Cortana mailbox is set up in the organization’s tenant so all the data is securely kept in the organization's Microsoft Exchange Online. When human assistance is needed, Scheduler creates a ticket with a specific team within Microsoft Support, this team is Microsoft Supplier Security & Privacy Assurance certified for personal and highly confidential information. The ticket enables access to the meeting details and Cortana’s conversations only for the meeting that requires assistance, this team can then guide Cortana to the appropriate next steps to schedule the meeting. During this time, all data remains securely within the organization’s Microsoft Exchange Online and the support team can only view the meeting details for the specific meeting in question via a separate UI with the associated ticket.


Scheduler is the first artificial intelligence service with human assistance in Microsoft 365 that allows Cortana to work without specific keywords, and, by delegating your meeting scheduling to Cortana we hope you will be able to save time and focus on the high-value work only human ingenuity can do.


Starting today, you can get Scheduler and get back valuable time for your organization.

  1. Learn more about Scheduler and useful information in the Product and description page
  2. Learn more about the Pricing for Scheduler and how to purchase it
  3. Learn how to set up the mailbox and enable the service with the Admin documentation

As always, we love reading your feedback – so please, let us know your thoughts!



Gabriel, @Charles Lee, and @Joey Wu


*Although we recommend to use Cortana as the assistant and the mailbox name, admins can set up the Scheduler mailbox with their preferred name.


Is it available in GCC?  If not, is there a timeline?

Senior Member

Pricing is insane....this will go nowhere...

New Contributor

@RichBean I guess that depends on if that $10 license is on top of the $10-$60 license you need for the mailbox or if it is for every user internal and external that interacts with it. I hope we get the same clarity with Windows announcement in two weeks.



I think there is a typo in the pricing page.  No way this is worth $10 / user / month!

Occasional Contributor

O365 E3 costs $20/u/mo how is calendar scheduling alone worth 50% of that?  Is this the same thing as  Does that free service get disabled?

New Contributor

Hmm. You'd have to pay me $10 a month to switch that Cortana on!


I wonder who got their way with this pricing model. Maybe fire them? ;)


Our organization will continue using Microsoft FindTime which is free. This new scheduler service is not worth the additional cost. 

New Contributor

The pricing on this is interesting.... Not sure Microsoft took the right approach.  I can see the argument that $10/user/month is cheap compared to hiring an assistant.  That said, I don't think this product does (or will ever) completely replace the need for an assistant.  I also understand the value proposition for owning your own data.  Even so, I can't see any company willing to pay $10/user/month to license all their users.  They are more likely to just license exec/managers/etc...  Why is Microsoft taking a scalable technology and targeting such a small niche?  Especially a niche that is unlikely to want/need this service.


The true target market for this service should be employees who do not have a personal assistant.  They can't purchase the license themselves and there is no way an org would justify licensing all staff.  Maybe charge per meeting scheduled or flat fee at the tenant level?  Or buddle into E3 or E5 to incentivize upgrading SKU's?

Free alternatives (FindTime/Cortana) > $40,000/year just for 'owning the data'. Hmmmmm

Senior Member

Nope, nope nope. I pay Microsoft tons of money per user for E5 licenses. No way I'm adding $10 per user per month to add Cortana scheduling. Absolute money grab for something that should be included in our licenses already.

I've been using Scheduler since very early in its preview. As much as it has saved me time and effort there's no way I'd pay an additional $10/user/month for it. Why not? The NLP still needs a bit more debugging (I think they fixed the confusion between "Jan" as a name and not just an abbreviation for "January" but that was a PITA), and it is far too quick to give up when it sees what it thinks as a conflict between calendars in widespread time zones. I still have a recurring problem with recurring meetings (scheduled instance-by-instance) that it will absolutely NOT turn into a Teams meeting no matter how many times I tell it to do so.

For free, I'd turn it on for every user, no questions asked. For something like $2/user/month, I'd recommend it for my key users. At 50% the monthly cost of an E3? No way. My users will burn more than $10 of time per month trying to figure out how to enable DWIM (do-what-I-mean) mode.

Occasional Visitor

Is this application fully available as of 6/8/2021

Senior Member

I've used the preview for a while and it's useful, got it's own problems. Really interested to find a confirmation on pricing - doesn't make sense as others have said.

Regular Visitor

This was a cool product until I looked at the pricing. :(

New Contributor

So, I signed up for a trial to see if it was worth, as many have said, the premium price tag. Having some significant issues getting it to schedule appointments for timeslots I want, so I opened a support ticket and was essentially told, there's no (included/free) support!!!!


Anybody know how/where I can raise my issues and actually get them looked at by a Microsoft Cortana Scheduler related person or team?

Occasional Visitor

Can the Cortana mailbox be a Shared Mailbox, or does it need to be a User Mailbox. If so, what license is required. Will this mailbox also need a Scheduler license assigned?

Senior Member

Sorry- I have to pay for Cortana (is it an add-on or part of an existing M365 subscription?) - if it's an add-on, I will simply use Microsoft FindTime for free. FindTime – The easiest way to schedule across companies (


Did someone look at Calendly and think we will charge $2 less than their Professional subscription? What's happening in Redmond- will we have to pay for Microsoft Editor in Word next?

Occasional Visitor

Hi, is it Scheduler capable of scheduling query in Devops and saving CSV file in shared folder or Teams?

New Contributor

Can we get an update as to what the official development and pricing of this is?  As a $10 addon, this is disturbingly laughable pricing, considering the value-add and comparative free options even offered with Microsoft.  I still have people using as well as Findtime and this offering doesn't come anywhere near the value.


I realize that this could fall into the category of "if you don't need it don't buy it, obviously" but it has such incredible potential that I don't want it to die on the vine and with no updates or responses here it's easy to believe that somehow this was a mistake.

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