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Why does constrained decoding break on token boundaries, and how do you handle the edge cases?

Grammar-constrained decoding sounds like a solved problem until tokenization misaligns with the grammar. The signal is the token-vs-character boundary mismatch and how prefix automata and token healing fix it.

Updated Aug 2026 · Grounded in real Applied AI Engineer interview loops and written to a senior-engineer editorial bar.

Grammar-constrained decoding sounds like a solved problem until tokenization misaligns with the grammar. The signal is the token-vs-character boundary mismatch and how prefix automata and token healing fix it.

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