Copilot Gets Smarter in Outlook: Automatic Conflict Resolution for 1:1 Meetings

Copilot in Outlook is getting an upgrade as a scheduling assistant. Soon, those with a Microsoft 365 Copilot license will be able to have Copilot automatically resolve simple scheduling conflicts that arise by rescheduling those activities at preferred times.

This will be rolling out to targeted release throughout the second half of this month and is specifically focused on scenarios like 1:1 meetings where they recur regularly but you might not be so concerned about exactly when they take place.

For me, this seems like another really good upgrade for Copilot to just lessen the load of an annoying task. However, exactly how helpful this is will depend on details of how this will work that, as yet, have not been communicated in the brief message center entry (MC1184999).

First, my assumption is this only works in scenarios where participant calendars are visible. It also specifically calls out 1:1 meetings, so likely its currently limited to two participant meetings. Last, it's unclear what those changes look like. Having worked in roles where I've needed to attend a lot of 1:1 meetings, I know that very often changes to these schedules are driven by fairly complex calendar needs, and the insights human assistants bring to resolving calendar chaos are very valuable. Just how big a bite of this apple will Copilot be able to take with this new feature?

This is an exciting new path for Copilot to start down, and the various improvements around it interacting with Outlook calendars over the last couple of months show a clear direction for how AI might transform business scheduling.

First posted on Linkedin on 11/13/2025 -> View Linkedin post here