Can't open private window from taskbar anymore

Do you use ‘CCleaner’ by any chance? Some searching turns up a suspicious confluence of users of that tool, and this issue.

Outside of that, here are some links that might help. YMMV.

https://support.google.com/chrome/thread/14579131

https://www.reddit.com/r/TronScript/comments/dsnsod/solution_to_incognito_mode_disappear_from_right/

If I were in your position, I would try the following:

  • Remove the pinned browser icon on your Taskbar
  • Disable the ‘Show recently opened items in Jump Lists…’ Windows setting
  • Re-pin Brave to your Taskbar
  • Re-enable the Jump Lists setting
  • Use Brave for a day or so and see if the other ‘Tasks’ in the right-click menu come back