Do Prompt Optimizers Break Requirements They Are Not Scored On? A Preregistered Study

Automatic prompt optimization (APO) uses feedback from model responses to improve prompts automatically. However, its effectiveness is usually measured through overall scores, which do not reveal which questions become correct, which previously correct answers become wrong, or whether improvements extend to unseen questions. We introduce Reflective Feedback-Driven Prompt Optimization (RFDPO), a tool that tracks recoveries (incorrect to correct), regressions (correct to incorrect), and churn (all changed outcomes). RFDPO uses this feedback to guide subsequent revisions and records prompt changes throughout optimization. We evaluate RFDPO across five benchmarks covering law, knowledge, instruction following, mathematics, and privacy, using GPT-5 as the optimizer and GPT-4o-mini and GPT-4.1 Mini as solvers. Our results show that overall accuracy can hide substantial changes: in five of nine configurations, churn was at least five times the absolute net change, and a single-item net change concealed up to 17 changed outcomes. Average validation gains were 7.9 percentage points, compared with 5.2 points on held-out tests. In a controlled ablation on LegalBench-Hearsay, item-level feedback reduced churn by 40% ($p=0.024$) while maintaining similar net gains. These findings motivate reporting recovery, regression, churn, and performance on unseen data alongside overall accuracy.

Automated prompt optimization methods (e.g., DSpy, TextGrad) can substantially improve the performance of large language model (LLM), however, their generalization ability across different tasks remains underperformed. In practice, the superiority of the optimized prompt on one benchmark often fails to transfer to another, and this limitation persists even when switching across different LLM backbones. To investigate the underexplored sources of heterogeneity in prompt performance, we conduct a causal inference-inspired observational analysis of optimized prompts across a diverse set of optimization frameworks, LLM backbones, and NLP benchmarks. To achieve the goal, we build upon the propensity-adjusted associational analysis together with multiple complementary representations of prompt edits, where the consistent task-conditioned edits patterns are identified. We find that complexity-increasing and meta-instructional edits are negatively associated with mathematical and multi-hop reasoning performance, whereas step-by-step and meta-cognitive edits improve logical and sequential reasoning tasks. These effects are robust across cognitive-load annotations, surface-level text features, and edit-motif analyses, and can generalize across optimization frameworks. Overall, these results indicate that prompt optimization failures arise from systematic interactions between edit families and task characteristics rather than random optimization artifacts, providing feature-level characterization of optimizer behavior and motivating future task-conditioned optimizer design.

Prompt optimization methods either analyze individual failures in isolation or compare prompt variants across examples, operating on single execution traces with no access to the reasoning process distinguishing success from failure on the same input. We introduce ContraPrompt, built on the observation that when a model fails but succeeds on a retry with feedback, the difference between its two chain-of-thought traces constitutes an optimization signal not captured by prior methods. Unlike prior contrastive methods, we compare complete intermediate reasoning processes: the two traces share model, input, and base prompt, so remaining differences reflect reasoning strategy and appended error feedback -- we call this dyadic reasoning trace analysis. The multi-attempt solving phase is an instrumented agentic retry loop that generates contrastive data automatically without human annotation. Extracted rules are organized into an input-aware decision tree routing instructions by observable input characteristics. On four reasoning and compliance benchmarks, ContraPrompt outperforms GEPA (Agrawal et al., 2026) on all four, with absolute gains of +8.29 pp on HotPotQA (+20.8% rel.), +2.21 pp on GDPR-Bench (+18.2% rel.), +7.14 pp on GPQA Diamond (+10.6% rel.), and +0.74 pp on BBH (+0.85% rel.). Ablations confirm dyadic trace contrastivity is the critical component, with a -16% relative average drop upon its removal. On 53 EvalSet black-box optimization problems, ContraPrompt beats GEPA on 11, ties on 41, and loses on 1 at equal budget. On FiNER-139 financial named entity recognition (Loukas et al., 2022), ContraPrompt achieves +7.77 pp over the unoptimized baseline (+11.6% rel.) and +1.94 pp over GEPA (+2.66% rel.), with branch conditions aligning with standard US GAAP financial-instrument categories.