The boss flees after 4 turns and your party "wins" whether they kill him or not. A couple of neat things about this boss - Doing these missions take you directly to the boss fight - no dungeon shenanigans are involved whatsoever. He will either steal your trinkets and you can hunt him down (A Thief in the Night event), or the townspeople mention his location and you can hunt him down (Shrieker's Prize event). Later in the game there will be a boss named the Shrieker that appears via a town event. I've had to repeatedly fulfill the requirements for a number of them until they decided to unlock and this achievement was one of them.I did stumble upon a neat "trick" to unlocking this particular achievement, though. I've noticed that a handful of the achievements in this game can be finicky and not unlock when they should.
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