Instruction Stacking Collapse: A Benchmark and the Capability-Dependent Value of Prompt Compilation

Production prompts rarely carry a single instruction. One system message may require valid JSON, a word limit, three citations, and a fixed tone at the same time. We study how instruction-following degrades as such constraints accumulate. We introduce a benchmark that stacks 24 verifier-checked instructions, one to twenty at a time, and evaluate three production-tier LLMs (Claude Sonnet 4.6, GPT-5-mini, Gemini 2.5 Flash). Instruction-following degrades non-linearly: the follow rate falls from 96% to as low as 20%, driven by a structured and reproducible set of pairwise conflicts. A single "output JSON" constraint, for example, is jointly unsatisfiable with nine others. We then evaluate a training-free remedy: an instruction compiler that rewrites the stacked prompt in a single LLM call and is reused across queries. Its benefit is capability-graded. It recovers up to +11 points of follow rate for weaker models, which are also the models most often deployed at scale, while leaving stronger models, which already internalise the same structure, essentially unchanged. Cluster-robust tests, same-baseline controls, and a within-family scaling ladder attribute the gain to the rewrite itself rather than to additional tokens, reordering, or measurement headroom. We release the benchmark, verifiers, and cached runs for full reproduction.