I was on a Multiplayer server, when my leather boots broke from a Spider that jumped out from the trees and it gave me the message of "WeAreSurpassable has completed the challenge [Serious Dedication]" And since I was seriously confused, I saw that you needed to break a diamond hoe and not armor. People said it was bugged with tools, but I guess it's bugged with armor as well. I haven't seen anyone report this bug so, here it is.