A King, 1000 Bottles of Wine, 10 Prisoners and a Drop of Poison
Brett Berry

I don’t think you need quite as fancy a solution- It would suffice to select for each bottle of wine a unique set of 5 prisoners, and administer each bottle to only the prisoners in its set. C(10, 5) is much greater than 1000, so you shouldn’t run out of unique combinations, and after the prisoners die you simply check which bottle was tasted by only the 5 dead prisoners.

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