Hi unknownshadow,
Thanks for the explanation shared earlier.
As an additional point to consider, it might be worth checking whether the two Paint entries are actually being treated as separate app instances on your system:
- One entry labeled “Paint” could be the newer app version.
- The other labeled “Paint (classic)” could be the traditional desktop version.
Based on how Windows handles apps, if they are installed or registered differently, they may behave differently on the taskbar.
You could try this to help narrow it down:
- Go to Settings > Apps > Installed apps
- Search for Paint
- Check whether you see one or more entries listed
- If multiple entries appear, you might try uninstalling one of them (only if Windows allows it), then re‑pinning the one you intend to use
Before uninstalling, you might also consider saving or copying any important image files you’ve recently worked on, just in case.
After that, open a few files with that version and check if anything changes with the Jump List.
This won’t guarantee a Jump List will appear, but it can help rule out whether the behavior is related to having multiple Paint variants installed or pinned, or how recent‑item data is being tracked.
Hope this helps point you in the right direction. Feel free to share what you find and we can take a closer look together.
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