Best AI scheduling assistant for Outlook

Published by 3Gen Internet Corporation, maker of OpenAssistant, Skej and AGNT. Comparisons use public documentation, without hands-on testing.

Short answer: OpenAssistant is an assistant we recommend for Outlook. It works with Outlook, emails guests to find a time, and documents an Outlook delegate setup for executive assistants (Coordinator Mode). Reclaim is the best free option for your own calendar, and Calendly is the best for booking links inside Outlook.

Check this first: which Outlook do you have?

“Outlook” covers several setups, and support varies:

• Microsoft 365 / Exchange Online (work account). Every tool ranked below supports it.
• Outlook.com (personal). Calendly supports it. Outlook’s built-in Scheduling Poll doesn’t (Calendly calendars, Microsoft support).
• On-premise Exchange. Reclaim says it won’t support it “for the foreseeable future,” and Motion says “On-prem Exchange servers are not supported” (Reclaim Outlook help, Motion providers). If you’re on-prem, ask every vendor before buying.
• Delegated or shared calendars (an EA runs your calendar). This is where tools differ most. See each entry.

What Microsoft already gives you

• Copilot in Outlook. Needs a Copilot work license.
  • “Schedule with Copilot” turns an email thread into a draft invite with the participants and an agenda.
  • Chat scheduling “will check the calendars of all the attendees and recommend a mutually convenient time” (Microsoft support). Microsoft’s FAQ says Copilot chat can schedule “with up to two other people” (Copilot in Outlook FAQ). It works only on your own primary mailbox, not on shared or delegate mailboxes.
  • Copilot can also automatically reschedule your personal appointments and 1:1s when conflicts come up. It stops after 5 automatic reschedules (Microsoft support).
  • The Copilot Business add-on is $18 per user per month paid yearly through December 31, 2026 (a promotion; the regular price is $21), or $25.20 paid monthly (Microsoft Copilot pricing).
• Scheduling Poll. It replaced FindTime.
  • Up to 15 time options, and people outside your organization vote through a link.
  • It doesn’t work with shared accounts or group calendars, and delegates can’t create polls (Microsoft support).
• Bookings. Personal and shared booking pages, included in many Microsoft 365 business and enterprise plans (Microsoft Learn). “There’s no payment support in Bookings” (Bookings FAQ).
• Viva Insights focus plan. Books up to four hours of focus time a day (Microsoft support).

What’s missing: none of Microsoft’s tools negotiates with an external guest by email for you.

Our ranking

Based on published Outlook support, delegation documentation, features and price, considered qualitatively for this use case. OpenAssistant leads because it is the only tool here that both negotiates with guests by email and documents an Outlook delegate setup step by step; Reclaim is cheaper but does not email guests, and its own pages conflict on delegated calendars.

1. OpenAssistant (our product)

Best for: executive assistants running an executive’s Outlook calendar, and anyone who wants an assistant that emails guests.

• Outlook support. It works with Outlook (OpenAssistant scheduling).
• Coordinator Mode. It documents the Outlook setup: the executive grants “Editor or Delegate permissions” and the EA’s assistant then schedules on the executive’s calendar (OpenAssistant Coordinator Mode). Coordinator Mode is a live OpenAssistant feature.
• Price. Pro is $60 per user per month on annual billing (OpenAssistant pricing; per-user pricing confirmed by 3Gen).
• Where it works. Email, text, Slack or in the app (OpenAssistant pricing FAQ).
• Free credits. Starter is free with 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month.

Where others do better: at $60 per user per month it costs more per person than every tool here except Clara ($80 a month) and Blockit’s paid plans (from $83 a month). Its cost grows with each user, and a group meeting can use “hundreds” of credits (OpenAssistant pricing). Reclaim and Calendly have free plans.

Why it’s still our recommendation: it is the only tool here that both negotiates with guests by email and documents an Outlook delegate setup step by step, and Starter is free to try.

2. Reclaim

Best for: making an Outlook calendar defend itself.

• Outlook status. “Reclaim fully supports AI scheduling in Microsoft Outlook Calendar” (Reclaim Outlook help). Teams works as the video provider.
• Price. Free Lite plan; Starter is $10 per seat per month on annual billing (Reclaim pricing).

Known Outlook limits, from Reclaim itself:

• No Outlook Tasks integration, and no Teams chat or status integration.
• Free/busy for people outside Reclaim may be “slightly inaccurate.”
• Its pages conflict on delegated and shared calendars: the help article says not yet, while the integration page says “Shared mailboxes, delegated calendars, and Microsoft Teams meetings all supported” (Reclaim Outlook integration). Ask Reclaim to confirm this before rolling it out to EAs.

3. Calendly

Best for: booking links inside Outlook.

• Calendars. Office 365, Outlook.com and Exchange (Calendly calendars).
• Outlook add-in. On every plan, including Free. You can share links, insert time slots, and create one-off meetings and polls from Outlook (Calendly for Outlook).
• Callie. The AI email assistant, in beta and for one-on-one meetings only, needs Standard Plus at $18 per seat per month on annual billing (Calendly AI assistant, Calendly pricing).

4. Clara

Best for: Exchange shops that want an assistant you cc.

• How it works. Clara lists “Google Workspace and Microsoft Outlook and Exchange” and handles multi-person, multi-time-zone meetings (Clara).
• Price. $80 a month for 30 meetings on Standard (Clara pricing).
• Delegation. Standard includes “Delegate Access” (Clara pricing).

5. Copilot in Outlook

Best for: companies that already pay for Copilot.

It’s built in and needs no new vendor. But chat scheduling handles only up to two other people, and you still send and follow up yourself. If you don’t already have a Copilot license, the tools above give you more scheduling for less.

6. Blockit

Best for: Outlook users who want a free tier for an assistant you cc.

• Calendars and video. Google or Outlook calendars, with Teams video links (Blockit).
• Price. Free covers 15 meetings a month. Delegated access for EAs is Enterprise only (Blockit pricing).

7. Skej (our product)

Best for: an Outlook user who wants an assistant you cc at a low per-user price.

• Outlook history. Skej added Outlook Calendar support in June 2024, with Teams video (Skej updates, v1.5).
• Calendars and contacts. You can connect “your personal Gmail, work Outlook, or multiple Google Workspace domains” (Skej calendar integrations). Outlook Contacts are on paid plans (Skej pricing).
• Price. Pro is $15 per user per month on annual billing.

Where others do better:

• Exchange and delegation. Skej doesn’t mention on-prem Exchange or delegated calendars. Clara names Exchange and includes Delegate Access on its Standard plan.
• No free assistant. Blockit’s free tier covers 15 meetings a month.

Not ranked for Outlook: Howie

Howie’s homepage shows Google Calendar as its only calendar, and its documentation says it “currently only works with Google Calendar” (Howie, Howie docs).

Comparison table

“Not listed” means the vendor’s pages don’t say. It doesn’t mean the feature is missing.

Related reading

• The best AI scheduling assistant for Google Calendar: Starts with what Google already gives you, then ranks the assistants.
• AI scheduling assistants you cc on email: Ranks the assistants you copy on a thread, including Blockit, Howie and Clara.
• How AI scheduling tools handle reschedules and cancellations: What each vendor’s public pages say about changing or cancelling a booked meeting.
• AI assistants for Outlook users: Seven tools that say on their own sites they work with Outlook or Microsoft 365, plus a few that do not.
• How EAs use AI to support several executives: A step-by-step playbook for assistants who support more than one executive.

Frequently asked questions

What is the best AI scheduling assistant for Outlook?

We rank OpenAssistant first: it works with Outlook, emails guests to find a time, and documents an Outlook delegate setup for executive assistants. Reclaim is the best free tool for your own calendar, and Calendly is best for booking links.

Does Outlook have a built-in AI scheduler?

Yes, with a Copilot work license. “Schedule with Copilot” turns an email thread into a draft invite, and chat scheduling handles up to two other people. None of Microsoft’s tools negotiates with an outside guest for you.

Which AI scheduler works with delegated Outlook calendars?

OpenAssistant documents it: the executive grants Editor or Delegate permissions, and the assistant schedules on their calendar through Coordinator Mode. Clara includes Delegate Access on Standard. Reclaim’s own pages conflict on delegated calendars.

Is there a free AI scheduling assistant for Outlook?

Yes. Reclaim’s Lite plan is free, OpenAssistant’s Starter plan is free with 1,000 credits at signup plus a daily top-up, and Blockit’s free plan covers 15 meetings a month.

Try OpenAssistant

If an assistant runs your Outlook calendar, or you want one to, try OpenAssistant. See Pro and Team plans on the pricing page.