Pinning Files to their Corresponding Apps Already Pinned to the Taskbar

Windows 11 Pro

Version 22H2 (OS Build 22621.2861)

I have already managed to pin files, folders, and apps to the taskbar on this Windows 11 machine, so I don't need assistance with that. My current issue is different but related. I typically use Open Office to manage our bills through a custom spreadsheet I create annually. In the past, I could easily drag a new file over the Open Office app icon on the taskbar to add it to the pinned list, similar to what is shown in the attached image. However, this functionality no longer works, and the instructions I've come across only focus on adding new items directly to the taskbar instead of pinning them. Has this feature been disabled intentionally? The presence of duplicate icons on the taskbar is causing confusion, and I haven't been successful in attempting to change their appearance. Any assistance you can provide would be greatly appreciated. Thank you in advance for your help.