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Microsoft Plans May Outlook Overhaul Focused on Web App and AI

The plan signals a shift to a web-first Outlook with AI at its core.

Overview

  • Microsoft’s official 365 Roadmap lists a major Outlook update in May 2026 centered on the new web-based Outlook for Windows.
  • The company intends to phase out the classic desktop Outlook and the Windows Mail and Calendar apps in favor of the new app over time.
  • Calendar changes add colleague calendars in the left navigation, calendar groups, and multi-select of calendars and non-adjacent events for batch actions.
  • Mail tools gain sorting for flagged messages by status, start date, or due date, and Outlook on the web adds export of events as ICS files.
  • AI features expand with Copilot in the classic client for in-message summaries and Anthropic’s Claude planned for Outlook in beta.