Microsoft updates Windows 11 right-click menu and adds Cloud recovery

Microsoft began rolling out a Windows 11 preview update Oct. 29, 2026, that customizes the right-click context menu and adds a cloud-based recovery option.

The preview adds a “customize menu” button that controls which commands appear when users right-click. People can toggle built-in commands such as Send To and Create Shortcut, rearrange items on the main menu, and decide whether third-party extensions appear on the main menu or in its submenus. The older design hid familiar commands behind a top row of icons and a “Show more options” submenu.

The update also introduces Cloud Rebuild, a recovery option that reinstalls Windows 11 directly from the cloud by pulling the system image and drivers from Windows Update. It works even when the existing installation fails to boot and needs no custom recovery image or external media. Microsoft classifies Cloud Rebuild as a recovery option, but it behaves like a fresh install: existing applications and files are not preserved, though users can sanitize entire system drives before reinstalling.

KB5127936 is cumulative for Windows 11 versions 26H2 and 25H2 and will reach all devices through a gradual rollout before general availability. The preview also includes changes to Xbox mode and settings. Microsoft announced the update Oct. 29, 2026, the same day its quarterly financial report showed a continued decline in Windows license sales for new PCs.

WVTRA said declining PC revenue could reduce new Windows installations and make existing users more important to Microsoft’s business. The outlet also pointed to a continuing tension between Microsoft’s cloud-connected and AI-powered capabilities and users’ desire for a quieter desktop that does not promote additional services. Small operating-system problems become significant when they interrupt common tasks users perform repeatedly, and a confirmed software bug calls for a different response than an intentional design choice users dislike.

WVTRA said Windows 11 has drawn criticism over unwanted prompts, account requirements, advertising-like recommendations, integrated Microsoft services, and artificial intelligence’s growing role. WVTRA also noted that The Verge has reported that Microsoft is working to rebuild user trust in Windows and pointed to Ars Technica guidance on decluttering Windows 11 25H2, reducing unwanted noise, and disabling or removing AI-related features.

The company publicly committed in early 2025 to fixing Windows core issues after online outcry and the “microslop” meme.

SlashGear reported Sept. 2, 2026, that Windows 11 users can now place the taskbar on the left, right, or top of the screen, with the Start menu adapting when docked to the top. In left-aligned view, icons can align to the top or stay centered, and users can always show both icons and window labels. Windows Search now prioritizes local apps and files, labels results by source, and lets users turn off web and Microsoft Store results completely.

The Start menu offers section-level customization, and users can disable the Recommended section, Recent panel, and All section while resizing the menu. Microsoft removed Copilot buttons from Notepad, Snipping Tool, Photos, and the Widgets section; Notepad now offers a Writing Tools menu with AI options, and users can disable them in settings. Setup is faster with fewer clicks, ads, and Microsoft account prompts, and users can skip updates during setup and install them later. A point-in-time restore feature backs up the operating system, apps, and system files at regular intervals, and users can roll back the backup from the Windows Recovery Environment.

Yahoo Tech reported Aug. 4, 2026, on an open letter from Pavan Davuluri, Microsoft’s Windows boss, to the Windows Insider community. Davuluri promised more control over updates, a more intentional approach to AI, greater attention to performance and reliability, and UX enhancements after analyzing feedback from people who care deeply about Windows. He said Microsoft had focused on turning Windows into a billboard for its other products through promotions, nudges, cross-selling, account pressure, and subscription hooks. The company also lets users pause Windows updates for as long as they want in 35-day increments, selecting a resume date in Settings > Windows Update > Pause updates.

Microsoft introduced memory efficiency improvements, including a more efficient memory allocator for systems with 8GB and above that reduces the Windows memory footprint, and tuned WinUI 3 so apps built on it use less memory by design. The company also drove efficiencies across Chromium and Webview2 components and claims boot and logon times have improved, though it provided no benchmarks. Start, File Explorer, Search, and Snipping Tool are faster and more responsive, and File Explorer received foundational architecture enhancements for launch and navigation. Microsoft also addressed unstable transitions and blurry thumbnails in File Explorer Home and improved reliability across the Address Bar, file size formatting, keyboard navigation, and renaming.

BleepingComputer reported Oct. 30, 2026, that Microsoft fixed Always On VPN issues caused by the September 2026 security updates. Always On VPN runs in the background and establishes secure tunnels back to corporate networks for domain-joined, non-domain-joined, and Microsoft Entra ID-joined devices on Windows 10, Windows 11, and Windows Server. The failures happened with automatic protocol selection using IKEv2 and SSTP, leaving connections stuck in a Connecting state or displaying “The specified port is already in use.”

Microsoft first acknowledged the issue in a service alert to IT administrators in late September 2026 and had mistakenly flagged it as fixed in the October 2026 cumulative updates. The KB5127936 preview update includes the fix. Microsoft said, “This update fixes an issue that affects Always On VPN connections after installing September security update.” IT administrators can also work around the problem by changing the VPN profile from automatic protocol selection to SSTP only or IKEv2 only.

The October 2026 preview update also fixes an issue preventing non-admin users from connecting to devices via Remote Desktop when users enable Administrator protection.