Beyond Aggregate Accuracy: Item-Level Transitions in Prompt Optimization

Chinmoy Mitra, Tarek Mahmud

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…