An increasing number of NLP applications interact with large language models (LLMs) through black-box APIs, making prompt engineering critical for controlling model behavior. Recent Automatic Prompt Optimization (APO) methods iteratively refine prompts using model-generated critiques (often called textual gradients), but they predominantly optimize from failures and underutilize information contained in correct predictions, leading to instability and semantic drift. We propose TRAS (Textual Regularization with Aggregated Signals), a feedback-centric framework that is plug-and-play with existing APO search backbones. It retains the standard textual gradient signal from prior work for error correction and introduces a complementary textual regularizer derived from successful predictions to preserve beneficial prompt components. Because both signals are stochastic and can be noisy, we further introduce Monte Carlo Signal Aggregation (MCSA), which samples multiple gradients or regularizers and aggregates them into a single actionable directive, emphasizing consistent, actionable advice while filtering out outliers. Motivated by rapid model churn, we also formalize Automatic Prompt Migration (APM), the practical problem of adapting an expert prompt across model versions or API providers without losing critical instructions. Across standard APO and APM scenarios, our approach consistently outperforms strong baselines, yielding higher accuracy, faster convergence, and lower query cost, while substantially reducing the degradation observed under naive prompt migration.
LLM-based prompt optimization, which uses LLM-provided ``textual gradients'' (feedback) to refine prompts, has emerged as an effective method for automatic prompt engineering. However, its scalability and stability are unclear when using more data in training. We systematically investigate the potential and challenges of scaling training data in textual gradient descent. We show that naively scaling training examples is infeasible due to both explicit context-length limits and an implicit context wall, where long-context degradation yields diminishing returns. Inspired by prior wisdom in stochastic gradient descent, we propose Textual Stochastic Gradient Descent with Momentum (TSGD-M), which reweights updates through momentum sampling, using bootstrapped minibatch validation accuracy as importance weights over historical prompts. To stabilize TSGD and enable effective scaling within a limited context window, TSGD-M carries prior prompts information by \textit{dynamically} exploring the past top performing prompts without expanding input context length. TSGD-M integrates seamlessly into existing prompt optimization frameworks, including TextGrad, DSPy-COPRO, and AdalFlow, and achieves consistent gains across 6 benchmarks.
Large language models (LLMs) are highly sensitive to the prompts used to specify task objectives and behavioral constraints. Many recent prompt optimization methods iteratively rewrite prompts using LLM-generated feedback, but the resulting prompts often become longer, accumulate narrow sample-specific rules, and generalize poorly beyond the training distribution. We study this failure mode as prompt distributional overfitting and argue that it reflects a lack of representation control in discrete text-space optimization. We formalize this view through representational inefficiency, a dual-factor measure that decomposes prompt inefficiency into capacity cost and scope narrowness, attributing distributional prompt overfitting to their coupled growth during optimization. We propose TextReg, a regularization framework that realizes a soft-penalty objective through regularized textual gradients, combining Dual-Evidence Gradient Purification, Semantic Edit Regularization, and Regularization-Guided Prompt Update. Across multiple reasoning benchmarks, TextReg substantially improves out-of-distribution (OOD) generalization, with accuracy gains of up to +11.8% over TextGrad and +16.5% over REVOLVE.
Automatic prompt optimization (APO) improves language-model programs by revising prompts from task feedback, yet it typically holds its training data fixed. Repeatedly optimizing against the same instances confines feedback to weaknesses already represented in those data, leaving related failure conditions unexplored. We therefore view each failure as a dual signal: it indicates both how the prompt should be revised and what new training evidence should be synthesized. We introduce FORGE, a failure-guided framework that co-evolves prompts and training data. FORGE abstracts imperfect executions into reusable failure modes and synthesizes new training data through four complementary mutation strategies. Verified instances are fed back into prompt search, allowing updated prompts to expose the next data needs. Across eight heterogeneous benchmarks, FORGE improves the aggregate score over the unoptimized baseline by 16.52 percentage points and outperforms all evaluated APO baselines. The synthesized data also transfer beyond FORGE: in a transfer study, they improve all nine APO comparisons by 2--9 points and all three GRPO comparisons by 4--8 points under matched optimization budgets. These results establish failures as a shared interface between prompt optimization and data synthesis, and show the benefit of jointly adapting what a model is instructed to do and what it learns from.