Microsoft is quietly cleaning up one of Windows 11’s most visible annoyances: the File Explorer right‑click menu. The latest Insider build —
Windows 11 Insider Preview Build 26220.7271 — reworks the File Explorer context menu to reduce top‑level clutter by grouping less‑used actions into a new nested flyout called
Manage file, and by moving cloud provider options into their own provider submenus. This is part of a measured usability-first patch Microsoft is testing in Dev and Beta channels, and it’s already showing a tangible reduction in vertical menu bloat for many users.
Background
Windows’ context menu has been a long-standing usability battleground. Since Windows 11’s launch, the new visual style and the introduction of additional shell-level integrations have made the right‑click menu taller and more visually dense. On laptops with common 16:9 displays and higher scaling settings, that menu could dominate the screen when it appeared, creating friction for everyday file tasks and increasing the likelihood of mis-clicks. Microsoft has acknowledged the problem and is now experimenting with targeted reorganization rather than removing functionality outright. This change arrives as part of an incremental Insider release that bundles a number of improvements and experiments — from File Explorer preloading to Store library uninstall options. The File Explorer context menu overhaul is one of the smaller items in the changelog on paper, but it’s arguably one of the most visible day‑to‑day improvements for power users, office workers, and casual users alike.
What changed in Build 26220.7271
The new organization: Manage file flyout and provider submenus
Microsoft’s official notes describe a focused rework of actions surfaced in the File Explorer right‑click menu. The most important moves are:
- A new Manage file flyout consolidates previously scattered actions such as Compress to ZIP, Copy as Path, Set as Desktop Background, Rotate Right, and Rotate Left.
- Cloud provider options (for example, OneDrive’s Always keep on this device and Free up space) are now tucked inside their provider’s flyout rather than appearing in the menu’s top level.
- Send to My Phone has been repositioned next to cloud provider entries for a more logical grouping.
- Open Folder Location has been moved to sit alongside Open and Open with for faster access when jumping to a file’s container.
Microsoft explicitly notes that the “Manage file” label may change in a future update, which signals the company is treating this as an iterative UX experiment rather than a completed redesign. That iterative stance matters: it means Microsoft will adjust wording, grouping, and placement based on Insider feedback rather than locking users into a final layout immediately.
File Explorer launch preloading (optional)
Alongside the context menu cleanup, Microsoft is testing
preloading File Explorer in the background to reduce launch times. The experiment includes an option in File Explorer’s Folder Options under View —
Enable window preloading for faster launch times — which users can disable if they prefer not to participate in the preload behavior. This is a separate, performance‑focused change but complements the menu work by improving perceived responsiveness.
Why this matters: less clutter, faster workflows
The change is deceptively simple: group infrequently used commands and surface only the core verbs at the top level. But small UX wins like this compound quickly.
- Reduced visual noise: By moving peripheral actions into a nested flyout, the top-level menu becomes shorter and more focused on the primary verbs most people use.
- Improved discoverability over time: Grouping similar actions together (archive, path copy, rotate, background) encourages muscle memory and reduces pointer travel.
- Better small-screen behavior: On laptops or tablets with limited vertical space, the top-level menu will no longer obscure as much content, which reduces context switch friction.
- Cleaner cloud integration: Cloud sync options are now contextually tied to their provider, making OneDrive actions feel less like global clutter and more like provider-specific controls.
Windows Latest’s hands‑on testing suggests the new grouping reduces the vertical footprint significantly; they measured the context menu shrinking from a size that could previously cover
around 75% of the vertical screen on typical laptop aspect ratios to
roughly 50% in their tests. Microsoft itself hasn’t published a percentage reduction, so real‑world results will vary by display, scaling, and which third‑party context menu extensions are installed. Treat measured percentages as illustrative, not definitive.
Strengths: sensible, conservative, reversible
Microsoft’s approach in this build follows a few solid UX principles:
- Function preservation: Nothing essential is removed — options are reorganized, not deleted. Users retain the ability to access the same commands; they’re simply nested to reduce top-level clutter. That’s a low‑risk move.
- Incremental rollout: This is an Insider experiment, which gives Microsoft the ability to collect feedback and tweak the design before rolling it out more broadly.
- Contextual grouping: Putting cloud controls inside provider flyouts and reordering device‑to‑cloud commands (like Send to My Phone) makes logical sense and should improve cognitive load for users who frequently interact with cloud storage.
- User control: The File Explorer preloading option can be toggled off, showing sensitivity to power users and enterprise admins who need deterministic behavior.
These strengths point to a mature product team focusing on polish and ergonomics rather than only feature marketing. For many users the payoff will be immediate: fewer oversized menus, fewer accidental clicks, and a more focused context menu experience.
Risks and downsides: edge‑case friction and third‑party compatibility
No UX change is free of tradeoffs. The nested flyout approach, while cleaner for casual users, introduces potential friction for certain workflows:
- Extra clicks for power users: Users who regularly use commands like Compress to ZIP or Copy as Path may find an additional mouse movement or click is required compared to the previous top-level placement. For keyboard-first workflows this is less of an issue, but the change does increase the average number of interactions for those frequent tasks.
- Third‑party context menu integration: Historically, third‑party apps (archive tools, cloud clients, shell extensions) have had mixed experiences with Windows’ new context menu paradigms. Some utilities had to update to expose actions in Windows 11’s streamlined menu; others still appear only after selecting “Show more options” or use legacy handlers that live in the classic menu. This reorganization could hide third‑party items further down the chain unless those apps update their integration to the new model. That’s a compatibility risk for enterprise deployments that rely on custom shell extensions.
- Discoverability for occasional users: If someone only occasionally uses a particular command, nesting it removes clutter but makes the command less discoverable. Microsoft’s choice to label the flyout “Manage file” (subject to change) is an attempt to reduce that risk, but discoverability will depend on clear labeling and sensible grouping.
- Performance and reliability edge cases: Preloading File Explorer helps launch times but could have unexplored memory or edge-case interactions on low‑RAM devices, virtual machines, or constrained enterprise images. The toggle mitigates this, but administrators should test the behavior before broadly enabling it in managed environments.
In short, this is a pragmatic, low‑risk reorganization that trades a tiny amount of direct access for less noise and fewer accidental clicks for the majority of users — but organizations and power users should test and plan for minor changes to workflows and third‑party tool compatibility.
Practical implications for different user groups
For casual users and students
The effect will mostly be positive: shorter menus, less confusion, and a less visually overwhelming right click. The new grouping reduces the temptation to stare at an enormous column of actions and instead surfaces the primary verbs you’re most likely to use.
For small laptops and Chromebook‑style tablets
The change is particularly valuable on 13–14" screens and devices running higher scaling (125% or 150%). The context menu previously could cover most of the work area; nesting reduces that interference and speeds up simple file tasks. Windows Latest’s testing found a notable reduction in vertical space usage, though your mileage will vary.
For power users and developers
There will be a short adjustment period. Scripting and automation won’t be affected — keyboard shortcuts, context menu verbs, and command‑line operations remain intact — but frequent mouse-centric operations may feel slightly slower until habits adapt. Developers of shell extensions and utilities should test integrations with the new menu to ensure their most used actions remain easy to reach.
For IT admins and enterprise deployments
This change is eligible for testing now in the Insider Dev/Beta rings, but enterprises should treat it the same as any UI experiment: test in a staging environment, check for policy implications, and confirm that custom context menu handlers behave as expected. The presence of an explicit preloading toggle and Microsoft’s decision not to remove functionality makes this an easy change to accept, but compatibility testing is still recommended, especially for custom shell extensions.
How to test it now (Insider Preview)
- Enroll a non-critical machine in the Windows Insider Dev or Beta channel.
- Update to Build 26220.7271 or higher when it’s available for your channel.
- Right‑click files and folders in File Explorer to see the new Manage file flyout and provider‑specific cloud submenus.
- To test the File Explorer preload behavior, open Folder Options → View and toggle Enable window preloading for faster launch times.
- If you rely on third‑party shell extensions (7‑Zip, WinRAR, cloud clients, enterprise handlers), verify that their actions still appear in the places you expect; some may still require “Show more options” or an update from the vendor.
What Microsoft didn’t quantify (and what to watch for)
Microsoft’s announcement is deliberately light on raw metrics. The company describes the changes as “aimed at reducing the space taken by less commonly used actions” and highlights reordering and grouping, but it doesn’t provide a precise percentage of screen real estate saved or telemetry-derived time‑to‑action improvements. Independent testers have observed meaningful reductions in menu height on typical devices, but those figures should be interpreted as indicative rather than definitive. Expect Microsoft to refine the experience as more Insiders provide feedback. Key quantities to monitor in future updates:
- Official Microsoft telemetry or study results that quantify reduced mis‑click rates or improved task completion times.
- Vendor updates from major shell extension authors (7‑Zip, WinRAR, cloud providers) confirming support for the new context menu model or guidance for enterprise admins.
- Any accessibility implications, especially for keyboard navigation and screen reader compatibility, as nested menus can change focus behavior.
If such quantifiable studies or official compatibility notes appear later, they will provide a clearer picture of the practical gains and tradeoffs.
Long view: a UX-first signal from Microsoft
This change is small in code but large in intent. It signals that Microsoft is investing in
polish and ergonomics in Windows 11 — not just feature drop spectacles. Grouping and ordering are classic UX levers: they don’t require heavy engineering, but they do improve everyday productivity and reduce friction.
Expect similar clutter-reduction work elsewhere in the shell. Microsoft’s move to group cloud provider entries and to rationalize the order of device‑to‑cloud features suggests a broader pattern: take noisy, frequently updated areas of the UI and emphasize clarity, context, and user control. That could extend to other menus, the taskbar, and system UI elements over coming releases.
Recommendations for readers and admins
- Try the Insider build on a test machine to evaluate the new menu behavior and File Explorer preload option.
- If you manage enterprise images, mark shell extensions and custom context menu tools for regression testing.
- Encourage vendors of critical utilities to publish compatibility notes or updates for the new menu paradigm.
- For personal use, try the new layout for a week before deciding whether to revert to classic behavior (for now, legacy behavior is still reachable via Show more options or third‑party menu managers).
Final verdict
The Manage file flyout and provider submenus in
Windows 11 Insider Preview Build 26220.7271 are a welcome, pragmatic refinement. They keep functionality intact while prioritizing clarity and reducing the intrusive vertical span that has made Windows 11’s right‑click menu feel clumsy on smaller screens. The move shows Microsoft adopting an iterative UX approach — test, collect feedback, and refine — rather than a heavy-handed redesign. That’s the right play for a feature that touches millions of workflows every day.
There are legitimate tradeoffs: a small additional interaction cost for frequently used items and the potential for third‑party compatibility hiccups. But the update’s conservative nature — grouping rather than removing — and the presence of toggles for experimental features make it an easy change to accept for most users and manageable for IT teams to test.
Expect more polish in coming releases, and keep an eye on third‑party vendors for updates that optimize their context menu integrations with this new, cleaner approach.
Source: Digital Trends
Windows 11 is about to make your right-click menu less painful to use