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So I'm trying to go back and do some of the challenges. I went into chapter 2 and did the roof tiles, King Slime, and puzzle challenges. I go to the Status menu to check the list, and they still aren't checked. Do I need to replay the entire chapter and fight the boss to get them to register?
Do not meddle in the affairs of dragons, for you are crunchy and good with ketchup.
Completed challenges don't register until you go through the pillar of light at the ends of the chapters (or defeating the final boss in Chapter 4's case), so you'll have to beat the boss again if you haven't already in that save.