Practically No, because Windlass generally designed to pick up 3 or 3.5 shackles hanging vertically and this is almost equivalent to 100m depth. If you drop in more than 100m, windlass won’t be able to take the load of the shackles plus anchor when it is off the ground.

If by drop means let go then never.

If planning by walking back then as mentioned in other reply check windlass capacity.

Newer bigger ships might have that capacity.

Of course you can drop but sadly you will never be able to pick it up.