Microsoft has begun seeding a new Canary-channel test build of Windows 11 that plants AI-assisted image editing directly into File Explorer’s right-click menu. The experimental update, widely reported as Build 27938, surfaces a new “AI actions” sub-menu when you right-click common image formats, offering one-click access to Bing Visual Search, background blur, object removal, and background removal.

The move marks another step in Microsoft’s campaign to weave generative AI into the operating system’s shell, surfacing intelligence right where users manage their files rather than forcing them to open separate applications. It arrives alongside a returning notification-area clock that can show seconds and a new Settings page that tracks which apps have recently tapped into the OS’s generative AI models.

What’s new: AI actions in the right-click menu

The most eye-catching change is the AI actions sub-menu that appears when you right-click a supported image in File Explorer. Instead of launching a dedicated editor, you can now dispatch common editing tasks from the context menu. The reported actions at launch include:

  • Bing Visual Search – uses the image as the search query to identify landmarks, plants, products, people, or find visually similar images across the web.
  • Blur Background – opens the Photos app with automatic subject/background separation, letting you adjust blur intensity or refine areas with a brush.
  • Erase Objects – invokes Photos’ generative erase to remove unwanted elements from a scene.
  • Remove Background – launches Paint’s automatic background removal to create a one-click subject cutout with no background.

The supported file types are .jpg, .jpeg, and .png. More complex formats such as RAW, PSD, or TIFF are not reliably supported in these quick flows. The actions reuse existing first-party apps—Photos, Paint, and Bing Visual Search—rather than embedding entirely new editors into File Explorer.

How it works under the hood

The AI actions sub-menu acts as a launcher. When you select an option, it either passes the file reference to the target app (Photos or Paint) with the edit preloaded, or sends the image to Bing Visual Search and returns results directly. This approach keeps the feature lightweight, relying on apps that are already installed and frequently updated through the Microsoft Store.

Microsoft has not publicly documented whether each action runs locally on the device or in the cloud. Some operations may leverage on-device AI models on Copilot+ PCs (those with a neural processing unit), while others will fall back to cloud processing. That hybrid model raises important questions about latency, privacy, and data residency, especially for business users handling sensitive content.

For document-oriented Copilot actions—such as summarizing a Word file or comparing PDFs—processing currently happens in Microsoft’s cloud and requires both OneDrive storage and a Microsoft 365/Copilot license. The image actions in this Canary build are separate from those document features, but both are part of a broader effort to bring micro-workflows to the shell.

Beyond images: notification clock and generative AI settings

Build 27938 also resurrects the ability to display seconds in the notification-area clock. Users can enable it via Settings > Time & language > Date & time by toggling “Show time in the Notification Center.” If the toggle is not yet visible, the rollout may still be server-gated; advanced users can unlock it with ViVeTool using feature IDs circulating in the community, though that comes with the usual risks of early feature activation.

A more significant addition for privacy-conscious users is a new “Text and image generation” section under Settings > Privacy & security. This page lists third-party apps that have recently utilized Windows-provided generative AI models. The intent is to give users visibility and per-app control over which software can access on-device generation capabilities. For enterprises, this is a necessary first step, but IT admins will likely demand more granular Group Policy and MDM controls before the feature is production-ready.

Privacy, enterprise, and the cloud conundrum

The hybrid local/cloud processing model is the biggest unanswered question. If an image or document is uploaded to Microsoft’s servers for analysis, the privacy calculus changes dramatically for regulated industries or anyone dealing with confidential data. The Settings page shows recent activity, but it is not a full audit trail and does not confirm where the data was processed.

For IT departments, visibility alone is not enough. Organizations will need:
- Explicit policies to disable cloud processing for generative actions.
- Role-based access controls to determine which users can use AI actions in File Explorer.
- Robust logging for compliance and forensic purposes.

Until Microsoft publishes clear per-action locality guarantees and enterprise-grade manageability features, many businesses will treat the functionality as cloud-dependent and restrict it on managed devices.

The productivity promise

Despite the caveats, the practical benefits of embedding AI in File Explorer are immediate. Common micro-tasks that once required opening Paint, Photos, or a browser are now just a right-click away. Social media managers can remove a photobomber from a product shot in seconds. Researchers can perform a visual lookup on a screenshot without breaking their workflow. Everyday users will discover tools they might never have opened otherwise.

This “in-flow” productivity is key to Microsoft’s design philosophy for Windows 11. By placing AI actions where people already work—the file system—the company reduces friction and speeds up trivial but frequent edits. It’s a classic shell integration play, similar to how the taskbar or Start menu evolved to surface more contextually relevant options over time.

Known instabilities: a Canary build caveat

As a Canary build, this release is the most experimental tier of the Windows Insider Program. Users should expect bugs and regressions. Community reports and Insider notes highlight several fixes and known issues:

Fixes
- Improved reliability of “Reset this PC” in Settings > System > Recovery.
- Corrected dark-mode color issues for low-space drive indicators in This PC.
- Restored thumbnails for certain video files with specific EXIF data.
- WMI Registry scanning performance improvements.
- Fixed Task Manager freezes and some green-screen errors (CRITICAL_PROCESS_DIED) seen in earlier Canary builds.

Known issues
- Installation rollbacks with error codes 0xC1900101-0x20017 or 0xC1900101-0x30017 for some Insiders.
- Certain Settings pages may hang when scanning temporary files.
- PIX on Windows cannot play GPU captures until a PIX update is installed.
- Audio devices may show a yellow exclamation mark in Device Manager.
- Screen flickering in some browsers.
- Occasional UI inconsistencies due to server-side feature gating.

These stability notes underscore the risk of deploying Canary builds on daily-driver machines. Insiders are strongly advised to use dedicated test devices or virtual machines with a fresh backup before experimenting.

How to test the AI actions today

If you want to try the feature, you’ll need a Windows Insider device enrolled in the Canary (or possibly Dev) channel. After updating to the latest build, right-click a .jpg or .png file in File Explorer. If the server-side flag is enabled for your machine, you’ll see the AI actions sub-menu. Because of heavy server gating, not everyone on the same build will see the feature immediately.

For the notification clock, check Settings > Time & language > Date & time for the “Show time in the Notification Center” toggle. If it’s missing, you can wait for the staged rollout or, with care, use ViVeTool to force-enable the feature ID.

Before testing, make sure your Photos and Paint apps are updated via the Microsoft Store—the Explorer actions rely on their latest versions. For document Copilot actions, you’ll need a Microsoft 365 account with Copilot entitlements and files stored in OneDrive.

A strategic direction, not just a gimmick

The arrival of AI actions in File Explorer is not a one-off novelty. It aligns with a clear strategic pattern: Microsoft is embedding AI throughout Windows 11 rather than confining it to a single app like Copilot or Edge. The pattern unfolds as:
- Surface AI where users already work (File Explorer, OneDrive, taskbar).
- Provide transparency and initial controls in Settings.
- Gate heavier enterprise and document features behind Microsoft 365/Copilot entitlements.

The immediate goal is to eliminate friction for tiny tasks. The longer-term play is a set of system-level APIs and governance tools that empower admins and developers to build consistent, trustworthy AI experiences across the platform. Microsoft’s Flight Hub and Insider Blog remain the best places to track when these experiments graduate from Canary to broader release channels.

Final verdict and practical checklist

Embedding AI into File Explorer is a pragmatic, user-centered step. It will speed up countless small edits and visual searches for everyday users and content creators. But for enterprises and privacy-sensitive users, the hybrid processing model demands clearer documentation and stronger administrative controls.

If you plan to test Build 27938 or an equivalent preview:
- Run it on a non-critical device with a recent backup.
- Right-click a .jpg or .png file and check for the AI actions sub-menu.
- Test each action—Visual Search, Blur Background, Erase Objects, Remove Background—and note whether processing happens locally (fast, offline-capable) or requires cloud connectivity.
- Visit Settings > Privacy & security > Text and image generation to review recent app activity.
- Enable the notification clock seconds and test the flyout.
- Monitor Device Manager, Task Manager, and Event Viewer for any regressions.
- If exploring Copilot document actions, use a Microsoft 365 account with Copilot enabled and files stored in OneDrive.

Microsoft’s Canary build is a preview of what could soon become a standard part of Windows’ productivity fabric. Expect more policy controls, locality transparency, and staged rollouts before this functionality lands safely in production channels.