Microsoft has quietly added a new way to summon Copilot from File Explorer in the latest Windows 11 Insider Preview builds, but early testing reveals a significant flaw: clicking the Ask Copilot button often opens the AI assistant without passing along the file you selected.
The change appears in Release Preview builds 26100.8728 and 26200.8728, released on June 12, 2026, for Windows 11 versions 24H2 and 25H2. When you hover your pointer over a file on the File Explorer Home page, two action buttons now appear: "Open file location" and "Ask Copilot." While the location shortcut works as expected, the Copilot integration is hit-or-miss, according to reports from users who have been able to test it.
What Actually Changed in File Explorer
File Explorer Home has been gradually evolving into an activity hub, surfacing recent files, favorites, and recommendations from OneDrive and Microsoft 365. The new hover actions double down on that approach.
Instead of forcing you to right-click or dig through a toolbar, Windows 11 now exposes two quick commands when you hover over a file card on the Home page. The first, "Open file location," instantly opens the folder that contains the file — a welcome fix for a long-standing annoyance where Home shows you a file but doesn't tell you where it lives. The second, "Ask Copilot," is meant to send the file to Microsoft's AI assistant so you can ask questions about it, request a summary, or perform other document-centric tasks.
Both commands appear only on the Home page, not in regular folder views. That's a deliberate choice: Microsoft wants to reinforce Home as a launchpad for recent work rather than sprinkle AI buttons everywhere. The feature is also restricted to work and school accounts that use Microsoft Entra ID, and it is not available in the European Economic Area — a common exclusion for new AI features while Microsoft navigates regional regulations.
The initial documentation from Microsoft dated June 12 clarifies that this is a controlled rollout. Even if your PC is running one of the eligible Release Preview builds, you may not see the buttons yet. Microsoft released updated builds (26100.8942 and 26200.8942) on July 20, 2026, which may expand visibility, but the company hasn't provided a timeline for broad availability.
What It Means for You
For most home users, nothing right now. Because the feature is tied to Entra ID accounts, your personal Microsoft account won't trigger the Copilot button. If you are part of a work or school organization that participates in the Windows Insider Program and your device runs these Release Preview builds, you might encounter it — but only if your administrator hasn't disabled it and the server-side rollout flag is active.
If you do see the button, the practical benefit is supposed to be speed. Instead of opening a document, manually launching Copilot, and attaching the file, you can start the conversation directly from File Explorer. But early hands-on reports, first flagged by Neowin, suggest that clicking Ask Copilot often just opens the Copilot app with an empty chat. The file doesn't appear in the conversation, forcing you to attach it manually — precisely the extra step the shortcut was designed to avoid.
That failure undermines the entire premise. A contextual AI button is only useful if it preserves context. When the handoff breaks, the button becomes little more than an alternative app launcher, adding visual clutter to a core Windows interface without saving time.
For IT administrators, this rollout raises more pressing concerns. The Ask Copilot button is a data-handling event: clicking it could send a file to Microsoft's cloud services, depending on how the back-end integration works. Managed organizations need clear controls over which files can be shared, under what conditions, and with which Copilot endpoint (enterprise-protected vs. consumer). Currently, Microsoft hasn't provided granular policy settings for this specific File Explorer action. The only available lever is the broader ability to disable Copilot entirely — a blunt instrument that many admins won't want to use.
How We Got Here
Microsoft has been experimenting with Copilot's place in Windows 11 for over two years. The assistant started as a sidebar, then became an app, then retreated from the taskbar into a resizable window. Along the way, the company peppered it into context menus, the Edge browser, Microsoft 365 apps, and even the taskbar's system tray. Each addition promised to make AI more accessible, but the cumulative effect can feel less like integration and more like a scattergun approach.
The File Explorer Home integration continues that trend. It follows a similar pattern to the "Ask Copilot" button Microsoft briefly tested on the taskbar earlier in 2025, which also struggled with context preservation. The company's strategy is clear: embed Copilot beside everyday objects so users never have to go looking for it. But the execution has often lagged behind the ambition.
The current builds arrive amid a broader effort to improve Windows 11's fundamentals. The same July wave of Insider updates includes a Cloud rebuild recovery tool, Taskbar position options, and smarter Windows Search prioritization. Microsoft appears to be balancing headline-grabbing AI additions with practical refinements, but the Copilot expansion in File Explorer feels like a feature that needed more time in the oven.
What to Do Now
If you're a Windows Insider on the Release Preview channel: You can check if the feature is active by opening File Explorer Home and hovering over a recent file. If you see the buttons, test them with a supported file (DOCX, PDF, image) and note whether Copilot actually receives the file. If the handoff fails, use the Feedback Hub to report the behavior, including your build number and account type. That data will help Microsoft improve the feature before wider release.
If you're a business or school user who encounters the buttons unexpectedly: Be cautious about clicking Ask Copilot on sensitive files. Until your organization confirms which Copilot service is being used and what data protections apply, treat the button as a potential data-sharing mechanism. Check with your IT department before relying on it for confidential work.
If you're an administrator: Start planning for how you'll manage this feature when it reaches general availability. Review your existing Copilot policies in Microsoft 365 and Windows. Consider whether you'll want to allow the action only for cloud-based files where compliance boundaries are clearer, or block it entirely for local and network storage. Watch for new Group Policy settings or MDM controls in the coming months; Microsoft often introduces them after the initial rollout based on early feedback.
If you don't want the feature at all: There is no dedicated off switch yet. The only guaranteed way to avoid it is to stay on the stable Windows 11 release track and not join the Insider program. When the feature does ship broadly, Microsoft will likely face pressure to add a simple toggle in Settings — much like it did for taskbar Copilot. Until then, you can reduce the visual clutter by customizing File Explorer Home to show fewer recent files or hiding recommendations, though that won't remove the buttons entirely if they're active.
What’s Next
The most important milestone will be whether Microsoft fixes the file handoff reliability. A dependable context transfer would transform the button from a broken promise into a genuine time-saver. Look for improvements in subsequent Release Preview builds, potentially through an updated Copilot app that properly receives shared content from File Explorer.
Equally critical is the rollout of enterprise controls. Without fine-grained policies, many organizations will simply block Copilot altogether — a outcome that hurts Microsoft’s AI ambitions more than a targeted control ever would.
Finally, watch for the feature to appear in non-Insider builds. Microsoft often uses Release Preview as a staging ground for features that ship in monthly cumulative updates, not just annual feature versions. If the company can iron out the handoff bugs and provide admins with the right levers, File Explorer Home could become one of Copilot’s most logical entry points. If not, it will join the list of AI shortcuts that looked good in a demo but failed to deliver in daily use.