Windows 11 24H2 Gets Smarter: Optional KB5058499 Update Adds Copilot, Click to Do, and New Share UI

Windows 11 24H2 Gets Smarter: Optional KB5058499 Update Adds Copilot, Click to Do, and New Share UI

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Written by Dave W. Shanahan

May 29, 2025

Microsoft has officially released the highly anticipated Windows 11 KB5058499 update for version 24H2, bringing a wave of new features, AI-powered enhancements, and essential bug fixes to millions of users. This optional cumulative update, now available as OS Build 26100.4202, signals Microsoft’s ongoing commitment to making Windows 11 a modern, intelligent, and user-friendly operating system.

Windows 11 KB5058499 Update: AI Integration Takes Center Stage

One of the standout aspects of KB5058499 is its deepened integration of artificial intelligence, particularly benefitting users with Copilot+ PCs—devices equipped with dedicated AI hardware. The update introduces smarter AI components for image search, content extraction, and semantic analysis, making everyday tasks more efficient and accessible. For example, Copilot can now parse natural language queries to help users locate system settings and generate richer image descriptions for screen readers, greatly enhancing accessibility.

Productivity Boost: Click to Do, Share UI, and Cross Device Resume

Windows 11 24H2 Gets Smarter: Optional KB5058499 Update Adds Copilot, Click to Do, and New Share UI
Click To Do (Image: Microsoft)

Click to Do receives a significant upgrade. Users can now highlight text or images and instantly send them to Copilot for actions such as summarization, rewriting, or creating bulleted lists. This feature streamlines workflows, whether you’re drafting emails, preparing reports, or organizing notes. The Click to Do enhancements are now available in the European Economic Area (EEA), with support for English, Spanish, and French—demonstrating Microsoft’s push for regional inclusivity and compliance with EU digital regulations.

The update also introduces a new drag-and-drop Share UI for the desktop. When users drag a file to the top region of the desktop, a new tray appears, allowing easy sharing to apps like WhatsApp or via the traditional Share UI. This reimagined sharing experience is designed to make file transfers and collaboration more intuitive and visually engaging.

Another notable addition is the Cross Device Resume feature. With this, you can seamlessly resume working on OneDrive files from your phone (iOS or Android) on your Windows 11 PC. If you were editing a file on your phone within the last five minutes before unlocking your PC, Windows 11 will prompt you to pick up where you left off, making cross-device productivity effortless.

Enhanced Graphics and HDR Controls

The KB5058499 update brings significant improvements to HDR management. Under Settings > System > Display, users will find a clearer label for the “Use HDR” option, better explaining which media types are supported. You can now stream HDR video even when HDR is turned off, and on PCs with Dolby Vision, a new toggle lets you enable or disable Dolby Vision independently of HDR, offering more control over your viewing experience.

Additional Features and Improvements

  • Copilot Enhancements: The Win + C keyboard shortcut now launches Copilot, and its function can be customized. Press and hold the Copilot key or Win + C for two seconds to activate “press to talk.”

  • Pen & Windows Ink: Click to Do can be added as a shortcut in the pen menu, making it easier to access for users with stylus-enabled devices.

  • Energy Saver: IT admins can now manage Energy Saver settings via group policies and Microsoft Intune, helping extend battery life and support sustainability goals.

  • Gamepad Keyboard Layout and Accessibility: Improvements to accessibility, including a gamepad keyboard layout and more informative PC spec cards in Settings.

Quality Improvements and Bug Fixes

KB5058499 isn’t just about new features—it also addresses a host of longstanding issues:

  • BitLocker: Fixes a bug where devices with BitLocker on removable drives could encounter blue screen errors after sleep or hybrid boot.

  • Graphics: Resolves problems where certain games became unresponsive after upgrading to 24H2.

  • Memory Leaks: Addresses increased memory usage in the Input Service, improving performance in multi-user and remote desktop scenarios.

  • Network: Corrects an issue where Windows Server 2025 would always show the network as “public” on new domain controllers, ensuring proper LDAP binding.

  • Multimedia and Camera: Fixes issues with Windows Hello Face Enrollment and camera previews in multi-app mode.

  • Boot Menu Screens: Fixes slow rendering of early boot screens, such as BitLocker PIN and Recovery key screens.

This update also continues Microsoft’s migration of legacy Control Panel functions into the Unified Settings app, further modernizing the Windows experience and simplifying device management for both everyday users and IT professionals.

Known Issues and User Guidance

Despite its many improvements, KB5058499 comes with a known issue: some users may notice blurry text in Chinese, Japanese, or Korean (CJK) languages when using Chromium-based browsers at 100% display scaling. Microsoft recommends temporarily increasing display scaling as a workaround while a permanent fix is developed.

How to Get the Update

KB5058499 is an optional, non-security preview update. Users can manually install it via Settings > Windows Update > Check for Updates, or download it directly from the Microsoft Update Catalog. If you have the “Get the latest updates as soon as they’re available” toggle enabled, the update may install automatically.

Windows 11 KB5058499 Highlights

  1. AI-powered Copilot enhancements and smarter search

  2. Upgraded Click to Do for text and image actions

  3. New drag-and-drop Share UI for easier file sharing

  4. Cross Device Resume for seamless OneDrive workflows

  5. Advanced HDR and Dolby Vision controls

  6. Energy Saver management for IT admins

  7. Accessibility and gamepad improvements

  8. Numerous bug fixes and quality updates

A Strategic Leap Forward for Windows 11

Windows 11 KB5058499 is more than a routine update—it’s a strategic step toward a smarter, more productive, and accessible operating system. With AI-powered features, enhanced productivity tools, and crucial quality improvements, Microsoft continues to evolve Windows 11 to meet the needs of both mainstream and power users. As future updates roll out, the deepening integration of AI and regional inclusivity will shape the next era of Windows computing.

Stay tuned to msftnewsnow.com for the latest updates and expert analysis on Microsoft’s evolving ecosystem.


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I'm Dave W. Shanahan, a Microsoft enthusiast with a passion for Windows 11, Xbox, Microsoft 365 Copilot, Azure, and more. After OnMSFT.com closed, I started MSFTNewsNow.com to keep the world updated on Microsoft news. Based in Massachusetts, you can find me on Twitter @Dav3Shanahan or email me at davewshanahan@gmail.com.