Pointless-Yet-Compulsive Pt. 3
I assume you mean that he is at level 19 in the castle, but it hasn't ticked off the requirement for the quest. I'd try getting him up another level. If it still doesn't trigger, then I'd contact customer service.
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Yes, that is what I mean. I believe when I upgraded him to level 16 it didn't update/get counted in the quest, but levels 17, 18, and 19 did. (I've rephrased the original message to hopefully make sense)