Microsoft is steadily expanding Copilot’s footprint in the desktop client, and the latest Outlook Classic AI feature rollout marks a clear shift toward user-initiated assistance rather than the always-on prompts that have frustrated power users. The company confirmed that a new highlight-driven tool called Explain This is arriving alongside a fully completed deployment of the master Copilot Settings menu.
#1 The new Explain This feature
According to an admin portal update (MC1311978) spotted by Windows Latest, Outlook Classic will now let you select any block of text inside an open email and immediately trigger Copilot to generate a contextual explanation. Rather than relying on generic dictionary definitions, the AI pulls directly from the surrounding message to tailor its response. If you are reading an IT dispatch about system crashes and highlight the acronym BSOD, Copilot will explain what it means specifically within the context of that message.
Microsoft explicitly designed the feature as a user-triggered action. You have to actively click the Explain This prompt after highlighting your text, meaning the AI will not auto-pop or interrupt your reading flow. This addresses a recurring complaint from enterprise administrators and privacy-conscious users who have pushed back against forced AI integrations in productivity suites. “This enhancement gives users greater control over when and how Copilot assists them, improving productivity, clarity, and decision-making directly within their workflow,” Microsoft noted in the admin portal update.
#2 How it works in practice
The implementation follows a straightforward selection-and-ask pattern. Once you highlight a phrase, a small floating prompt appears in the reading pane. Clicking it opens a Copilot-generated response panel that sits alongside the email without blocking your view. The feature does not require you to open a separate sidebar or navigate away from your inbox.
It is worth noting that this is not a standalone free tool. A valid Microsoft 365 Copilot subscription is required to activate Explain This. Users on standard E3 or E5 licenses without the Copilot add-on will not see the prompt, regardless of their Outlook build. The rollout is expected to finish by the end of September, with most tenants receiving the feature in early September depending on their update channel.
#3 Copilot Settings are now fully live
Alongside the new AI capability, Microsoft confirmed that the master Copilot Settings menu has finished rolling out to all Outlook Classic users. You can access it by clicking File in the ribbon and selecting Copilot Settings from the left navigation pane. This dedicated control panel centralizes every Copilot-related toggle in one place, replacing the scattered configuration options that previously lived across multiple menus.
The most important switch in this menu is the master Copilot toggle. When disabled, it suppresses all Copilot functionality within Outlook Classic, including the ribbon button, inbox summaries, and the new Explain This feature. This gives administrators and individual users a clean off-ramp if they prefer to keep AI out of their daily email workflow entirely.
#4 Draft Instructions and user control
The settings panel also introduces Draft Instructions, which remains disabled by default. When enabled, it allows you to feed Copilot specific preferences for how it should generate email drafts. You can specify your preferred tone, target message length, and even standard greeting or sign-off phrases. The AI uses these inputs as a persistent prompt, so generated drafts align more closely with your actual writing style rather than defaulting to a generic corporate voice.
New Outlook already offered a similar toggle, so bringing it to the classic client was largely a matter of parity. The feature is particularly useful for teams that rely on Copilot for drafting but want to maintain brand consistency or personal voice across all outgoing messages.
Why This Outlook Classic AI Feature Matters
If you manage a fleet of Windows devices or simply prefer to keep AI features opt-in, these updates are a net positive. The Explain This tool solves a real workflow friction point: decoding jargon, acronyms, or dense technical prose without leaving your inbox. Because it requires explicit user initiation, it avoids the notification fatigue that has plagued earlier Copilot rollouts. However, the requirement for a paid Microsoft 365 Copilot subscription means smaller organizations will need to budget for the add-on before they can leverage the feature.
How to get it
The Explain This feature and the updated Copilot Settings menu are rolling out through the standard Microsoft 365 update channels. Users on the Current Channel should expect to see the changes in early September, while those on the Monthly Enterprise Channel may see a slight delay. To verify your build and check for updates, navigate to File > Office Account > Update Options > Update Now. If you do not see the Explain This prompt after your next restart, ensure your tenant has the Copilot add-on assigned and that the master Copilot toggle remains enabled in File > Copilot Settings.
Source: Windows Latest
Over to you: Are you going to rely on the new Explain This feature for technical emails, or will you keep Copilot disabled for now?
You may also like
Microsoft Edge Ends Support for MV2 Extensions, Killing uBlock Origin and Older Add-ons
Microsoft Edge Begins Consumer Rollout of Manifest Version 3 Extensions
Windows 10 LTSC 2021 End of Support Confirmed: Here Is What You Need to Know
Windows Search Improvements Arriving in August Updates: What to Expect
