Classic Outlook for Windows: User-initiated insights with Copilot

Classic Outlook for Windows will add User Initiated Insights with Copilot, letting users highlight email text to get contextual AI-generated insights. Rolling out May-June 2026, the feature is on by default for eligible users, integrates into Outlook without add-ins, and follows existing Microsoft 365 security policies.

[Introduction]

We're introducing User Initiated Insights in Copilot for classic Outlook for Windows, enabling users to manually select text within an email and prompt Copilot to provide contextual insights. This enhancement gives users greater control over when and how Copilot assists them, improving productivity, clarity, and decision-making directly within their workflow.

This message is associated with Roadmap ID 508524.

[When this will happen:]

• Public Preview (Worldwide): We began rolling out in early May 2026 and expect to complete by late May 2026.
• General Availability (Worldwide): We will begin rolling out in early June 2026 and expect to complete by late June 2026.

[How this affects your organization:]

Who is affected:

• Users with Microsoft 365 Copilot capabilities
• Organizations using classic Outlook for Windows

What will happen:

• Users will be able to highlight text in emails and invoke Copilot to generate insights.

Screenshot: When text is highlighted in an email, an Explain This button appears to provide additional context:



• Functionality is built into the Outlook experience and does not require a separate add-in.
• The feature will be on by default for eligible users.
• Existing Microsoft 365 security, compliance, and data protection policies continue to apply.

[What you can do to prepare:]

• If you do not want users to access this feature, remove or restrict Copilot capabilities.
• Verify users are running the latest version of classic Outlook for Windows.
• Inform helpdesk and support staff about this new Copilot interaction model.
• Communicate to users how to select text and invoke Copilot for contextual insights.

Learn more:

• How do I enable or disable Microsoft Copilot on MS 365 Premium | Microsoft Learn
• Instructions to turn off Copilot | Microsoft Support

[Compliance considerations:]

Compliance area	Explanation
Introduces AI/ML capabilities interacting with customer data.	The feature enables Copilot to process user-selected email content to generate insights.
Provides a new way for users to interact with generative AI.	Users can invoke Copilot directly by selecting text within emails.
Allows users to enable or disable the feature at use time.	Users control invocation by choosing when to select text and engage Copilot.