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We study this question with LearnStop, a hidden-state-free checkpoint stopper for reasoning language models. At fixed budget checkpoints, LearnStop probes a short answer from the current reasoning prefix and predicts prefix correctness from online features such as answer confidence, entropy, prefix vote share, answer stability, and backtracking-marker density. Across 18 task-model settings spanning GSM8K, MATH-500, MMLU-Pro, AIME-90, GPQA, Qwen3, and DeepSeek-R1 distillations, the answer is task-dependent. On free-form math, learned multi-feature stopping improves the fixed-budget frontier and often beats scalar exits: on GSM8K with Qwen3-32B, the empirical frontier reaches a post-hoc peak adapt gain of +0.157, validation-selected operating points p","title":"When Does Learning to Stop Help? 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