You roll a die repeatedly and may cash in the running total at any time, but you lose everything if it ever lands on a perfect square. When should you stop?
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You roll a fair six-sided die repeatedly and keep a running total, which you may cash in at any time. If the running total ever hits a perfect square (1, 4, 9, 16, ...) you lose everything. What is the optimal strategy for when to stop?
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