How to "pocket autopickup settings?"

I was, and still am, really confused by the pocket autopickup system. How does it really work?
Example: turrets hit my “US Ballistic Vest > 4 items” and shatter one of the “ESAPI Ballistic Plate”. I have “shattered ceramic front plate” blacklisted, why isn’t the item unloading?

additionally, how do you get autopickup to work from contained items? I spend a bunch on vending machines (especially buying plutonium fuel cells) and I find it a hassle to manually unload each wallet I find… Is there a way to enable autopickup inside items? It doesn’t work on zombies, and instead just re-picks-up the zero-money cash cards I try to drop after emptying them. “cash card*” should be the right syntax, am I wrong?