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Microsoft fixed 'Open with' Windows 10 taskbar bug in KB5039299

A late prototype of the Windows 10 stock wallpaper found in a leaked Windows 11 build

While most users probably ignore optional non-security updates for Windows 10 and 11 as they are not mandatory, sometimes, it is worth installing the latest preview release, especially when it fixes a specific annoying bug. That is the case with KB5039299, which was just released for Windows 10 version 22H2. It resolves a confirmed taskbar issue where right-clicking an app and an attempt to select something from its jump list would result in the "Open with" dialog showing up instead.

Microsoft has now assured that the bug is resolved in KB5039299:

This update addresses a known issue that might occur when you right-click some apps. Instead of running the task you choose from the context menu, an “Open with” dialog appears. It asks you, "How do you want to open this file?" This issue might affect any app that has tasks on a context menu. This issue also affects the icons on the taskbar and Start menu.

This update addresses an issue that affects an app’s jump list on the taskbar. Completing actions from that list might fail. A jump list is a menu that appears when you right-click an app on the taskbar or Start menu. It gives you quick access to recently or frequently used app items.

Microsoft is still working on fixing several open bugs in Windows 10 version 22H2. For example, you still cannot change the profile picture for local accounts; Copilot does not work if you have the taskbar anywhere but its default position; Microsoft Connected Cache is broken; and there is the 0x80070643 error. The company says fixes for those issues will be available in future updates, except for the 0x80070643, which requires manual fixing.

You can download KB5039299 by heading to Windows Settings > Windows Update and downloading available optional updates. You can also get the update from the Microsoft Update Catalog and install it manually. Check out full release notes with other improvements in KB5039299 here. If you are a Windows 11 user, details about its latest non-security update are available here.

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