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When you complete a quest task that you kill/sink a target and need to search for an item it sometimes just doesnt find what you are looking for (yesterday i had to sink 5 navy ships before i found who i was supposed to find on board) i am guessing they add a probability percentage to find said item/person when the task is done, so sometimes you wil find it every time, while others may need to complete the task again ... its all based on probability percentages.
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Pirate name: Bad Pete
  
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