Classic Outlook gains on-demand Copilot text analysis
Microsoft is adding User Initiated Insights to Classic Outlook for Windows. Users can now highlight any text in an email and ask Copilot for contextual analysis without installing extra tools. The feature starts rolling out in May 2026 and reaches most eligible users by June. It follows existing security policies and requires no administrator changes. Public preview began in early May. The update targets the desktop version many mid-sized companies still run instead of the newer Outlook app.
Before this change, anyone wanting Copilot help inside Outlook had to switch to the new app or accept that the feature lived only in preview builds. Most office coordinators kept using Classic Outlook because it preserved their rules, add-ins, and folder views, so Copilot stayed out of reach. Now the tool appears inside the version they already open every morning. The risk is that without a clear workflow the new option simply becomes one more button to ignore or another source of low-value suggestions that compete with actual email triage.
Analysis
Run a two-day test on three real emails where you highlight only the decision or action line, then turn the feature off if the output does not save you at least one minute per message. Do not leave it enabled by default.
Citation
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