Drop from the tube into the shell plate?
Make sure the shell plate is perfectly flat and the center nut is tightened so there is no vertcal play in the shell plate, some resistance in rotation is good.
When loading, make sure the operating handle has bottomed. Bottoming has a unique feel and with practice, it will become habit.
To adjust the primer feed for a perfect primer drop every time, adjust the primer seating punch first (assuming you have the resizing die perfectly
adjusted per the 366 manual). Generally, the primer feed stop unit fingers will have a noticeable bulge-out when adjusted correctly as the handle bottoms. The adjustment is quite sensitive: adjust no more than a 1/4 turn and test.
Drop from the shell plate into the seater?
You have to raise the operating handle slowly. The primer drops into the seater by gravity. Hornady marketed the gas assist to slow the shell plate down, disconnecting the shell plate from the operating handle on the upstroke.
If you are sizing high brass, the handle will jump as the hull is released from the sizer, usually just as the primer drop is about to happen causing the fresh primer to catch between the shell plate and the seater. You can adjust the deprime punch guide down to kick the hull out of the sizer sooner.
The deprime punch guide can be adjusted to a more comfortable place on the upstroke. The proper place is at the lowest point where the primers are knocked out totally reliably—about a 1/4". This point will insure the deprime punch guide centers the deprime rod in the hull's flash hole.