Microsoft is testing a new way to launch the Copilot AI assistant directly from File Explorer Home in Windows 11, but early reports from the Release Preview channel indicate the feature can’t yet do the one thing it’s supposed to: attach the file you selected. Instead, clicking ‘Ask Copilot’ opens a generic Copilot chat window with no context about the file, leaving users to manually hunt down and reattach the document—defeating the purpose of the shortcut.

What the Feature Is Supposed to Do

The idea is straightforward. In File Explorer’s Home page—the landing screen that shows recent, recommended, and frequently used files—hovering over an eligible file card can now reveal a small set of quick actions. Alongside the genuinely useful ‘Open file location’ shortcut, you may see an ‘Ask Copilot’ command.

Select it, and Copilot should launch with that file already attached or otherwise available as conversational context. From there, you could ask the assistant to summarize a document, extract key dates, explain an error in a screenshot, or compare two files. The whole point is to avoid the extra steps of opening the file, switching to Copilot, and manually attaching it.

The feature appears only on File Explorer Home, not in every folder, and only for certain file types surfaced as recommendations or recent items. Microsoft is deploying it gradually, so not every Release Preview device shows the option yet.

Why It’s Breaking Right Now

According to testing first reported by Neowin, selecting ‘Ask Copilot’ on a file currently does nothing more than open the Copilot app in a blank state. The selected file is not attached, identified, or even referenced in the new chat. You’re left staring at an empty input box, exactly as if you’d launched Copilot from the taskbar.

That’s a critical failure for a contextual command. Without the file handoff, the shortcut adds no value. Worse, it introduces ambiguity: you can’t tell if the file was sent invisibly, if processing failed, or if the button simply doesn’t work. For a feature that has been previewed in earlier Insider builds and is now in Release Preview—the last stop before production—this kind of basic wiring issue is disappointing.

File Explorer manages an enormous variety of content, from text documents and images to encrypted archives and proprietary formats. Not every file can or should be sent to Copilot. A well-designed integration would confirm compatibility, warn about size limits, and explain if a file is unsupported before launching the assistant. Right now, it does none of that.

Who Is Affected and How

For home users, the broken handoff turns a potential time-saver into extra friction. The feature might one day help you quickly summarize a long PDF, identify objects in a photo, or pull action items from a meeting note without opening the full application. But until it works reliably, you’re better off using existing Copilot ways: drag and drop a file into the app, or use the ‘Add a file’ button. Worse, the disjointed experience may confuse users who already struggle with Copilot’s shifting branding, subscription tiers, and varying capabilities across devices.

For power users and developers, the feature is likely to be ignored or met with frustration. These users know exactly where their files live and can launch Copilot with a keystroke. A shortcut that doesn’t actually attach the selected file is worse than useless—it’s another AI entry point to tune out.

For IT administrators, the immediate concern is governance. File Explorer touches everything—local storage, OneDrive, network shares, and managed content. If Ask Copilot eventually sends files to Microsoft’s cloud, admins need group policies to control or disable it, especially in regulated environments. Right now, there’s no documented way to manage this behavior with Intune or Group Policy. That means a potential data leak vector could arrive with a cumulative update, and help desks would have no clear guidance on how to respond. Without transparent handling of sensitivity labels, account boundaries, and enterprise data protection, the feature is a nonstarter for business use.

How Microsoft Got Here

Microsoft has spent years trying to weave Copilot into the Windows fabric. It started as a sidebar assistant in Windows 11, then became a standalone app decoupled from the OS so it could update faster. Along the way, the company scattered Copilot shortcuts across the interface: in the taskbar, Start menu, web search, Photos, Snipping Tool, and now File Explorer.

In March 2026, Microsoft publicly stated it would reduce unnecessary AI entry points and focus on “intentional, well-crafted” experiences. It then removed some Copilot buttons from Photos and Snipping Tool. Adding another one in File Explorer just a few months later seems at odds with that message—unless the company believes file analysis is a genuinely compelling use case.

The File Explorer shortcut itself isn’t brand new. Microsoft has teased similar hover actions in earlier preview work, restricting them by account type and region. Its appearance in Release Preview suggests the company sees enough promise to move it closer to general availability. But a buggy context transfer this late in the cycle undercuts that confidence.

What You Can Do Right Now

If you’re a Windows Insider on the Release Preview channel, you can help by filing feedback through the Feedback Hub. Reproduce the issue—hover over a file in File Explorer Home, select Ask Copilot, note whether the file appears attached. Clearly document what file type you used, whether you’re signed into a Microsoft 365 subscription, and which build you’re running. That data may help Microsoft understand why the handoff is failing.

If you’re a regular Windows 11 user, you don’t need to take any action. This feature hasn’t been released to the stable channel, and there’s no guarantee it will ship in its current form. Even after a cumulative update arrives, Microsoft often gates features behind controlled rollouts, so you might not see it for weeks or months.

If you’re an IT pro, start planning. While you can’t set a policy for this feature yet, you can review your overall Copilot governance: which users have access, what data they can share, and whether you’ve deployed the Copilot app or managed it through Microsoft 365. Prepare a communication plan so that when—or if—this button appears, employees know whether they should use it and what safeguards apply.

For everyone, the best way to use Copilot with files today remains the manual method. Open the Copilot app via the taskbar, click the attachment icon, and upload your file. It’s an extra step, but it works consistently and gives you clear control over what’s shared.

The Road Ahead

The next few Windows 11 cumulative updates, particularly for versions 24H2 and 25H2, will be telling. If Microsoft fixes the handoff so that selecting Ask Copilot visibly attaches the file and confirms what Copilot can access, the feature could become a modest but useful time-saver. If the company instead pushes it out broadly without resolving the context issue, it will reinforce the perception that Copilot integration prioritizes placement over practical help.

Beyond the basic bug, look for these signs of a mature rollout: documented support for specific file types and size limits, clear in-app disclosures about how your data is processed, enterprise policies that allow granular control, and—critically—a simple toggle to turn the feature off without disabling Copilot entirely.

Windows 11 users have learned to be patient with gradually unfolding features. But a button that claims to ask Copilot about a file must, at minimum, hand over that file. Until it does, this integration is little more than a shortcut to an empty chat window.