Contrastive Reflection for Iterative Prompt Optimization

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.

Large language models (LLMs) have become increasingly capable of following instructions and complex reasoning, making prompting a flexible interface for adapting models without parameter updates. Yet prompt design remains labor-intensive and highly sensitive to formatting, phrasing, and instruction order, motivating automated prompt optimization methods that reduce manual effort while preserving inference-time flexibility. However, existing methods often search over prompt candidates or use fixed critique-refine pipelines driven by individual examples or small batches, limiting their ability to capture systematic error patterns and make targeted edits grounded in failure history. We propose Reflective Prompt Tuning (RPT), a framework that uses LLM function calling to simulate the iterative workflow of human prompt engineers. An LLM optimizer calls a diagnostic function that evaluates the target model over an entire optimization set, summarizes recurring failure modes, and returns a structured diagnostic report. The optimizer uses this report, together with an accumulated memory of prior reports, to revise the prompt for the next iteration. RPT further supports confidence-aware optimization by using calibration signals in diagnostic feedback and final prompt selection. Across three reasoning tasks, RPT improves over initial prompts by up to 12.9 points, remains competitive with state of the art, and improves confidence calibration. Our analyses show that RPT is especially effective on multi-hop and mathematical reasoning, producing targeted prompt revisions that align with diagnosed failure patterns and lead to gains in task performance and calibration.

Agentic search systems iteratively interact with retrieval models to answer complex queries. Despite substantial progress, optimizing retrievers for agentic search remains challenging, often requiring heavy co-training or gold-standard annotations that limit real-world applicability. We propose Critic-R, a framework that explicitly closes the feedback loop between the reasoning agent and the retrieval model during both inference and training. Critic-R introduces a critic model that evaluates the agent's introspective reasoning trace after consuming retrieved evidence to determine whether the retrieved context sufficiently supports the next reasoning step. Critic-R has two complementary mechanisms: Critic-R-Zero, an inference-time query refinement loop that iteratively rewrites queries and retrieval instructions, and Critic-Embed, an optimization approach for retrieval models that leverages successful and failed refinement trajectories as automatic supervision without requiring manual relevance annotation. We evaluate Critic-R on HotpotQA, 2WikiMultihopQA, MuSiQue, and Bamboogle. Results show that Critic-R significantly improves both retrieval quality and downstream answer accuracy.