For some reason it'll drop it's item when I delete it in creative mode, and by pushing it using a piston.

I was looking at the pictures you posted of this in #upgrade-aquatic and it looks like you're using a Quark block? Are you able to reproduce this bug without using that specific block?

Just tested, I think its definitely on our end, because in creative and breaking a bedroll makes it drop itself, so I think fixing that will fix this