Drag cursor not in sync with keyboard modifiers on macOS

Using automatic drag and drop doesn't update the cursor icon according to the keyboard modifiers. The buggy behavior even varies between 6.6.1 and 6.8.3. The proposed drop action is always correct based on the keyboard modifier. 

I've attached two videos to show the problematic behavior. One is for 6.6.1. I'm first entering the drop area and then press the option modifier for a moment. I released the option modifier before the drop, but the cursor still shows the plus sign and when I drop the drop action is actually move. Leaving and then re-entering the drop area seems to update the cursor.

On 6.8.3 the modifier has to be pressed before entering the drop area to show the right cursor. Pressing the modifier after entering the drop area doesn't update the cursor icon at all. Still the correct drop action is proposed. In the video I'm also entering first then press the modifier and drop which results in the correct copy action. In the second attempt I'm pressing the modifier, but released it before dropping it so it results in the correct move action.