When you fight Plant-typed creatures (that include Ents and Ancient Ents), the morale of the Blackthorn Crown drops by 20 points. Otherwise, it goes up by 2 for each encounter. I am not sure how things turn out when you encounter dryads with no plants in the first place.
The Blackthorn crown keeper fight is fairly easy probably due to the value of the item. It might be easier to suppress the keeper than to manage its morale.
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