Deactivate Upload File Cache
I save a screenshot as screenshot.png in my Downloads-Folder (Win). Then I upload this screenshot to a planner task - works fine so far.
I save another (different) screenshot as screenshot.png in my Downloads-Folder. In other words I overwrite the file. When I now upload the file in a (different) planner task, planner takes the file from cache => I have the wrong file in the task.