Textual-gradient methods automate prompt optimization through natural-language feedback, but their iterative updates can be unstable. We identify two sources of this instability: noisy gradients produced from already-correct examples and over-specialization to hard cases that degrades performance on simpler inputs. We introduce STEVE, a stabilization framework with two coupled mechanisms. Error-Driven Refinement generates gradients only from incorrectly handled examples, concentrating updates on informative failures. Regularized Verification treats every update as provisional and accepts it only when improvement on hard cases does not cause unacceptable regression on a preservation set. Across ten reasoning benchmarks, three evaluator/optimizer models, and established prompt-optimization baselines, STEVE reduces degradation and produces more robust prompts. Additional evaluations with gpt-5.4-mini/gpt-5.4 on symbolic reasoning, GSM8K-Platinum, and DS-1000 show that these gains persist with newer models and larger test sets. STEVE therefore provides a practical way to improve the stability and effectiveness of textual-gradient prompt optimization.
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.
Customizing an LLM judge to a specific problem or domain often involves optimizing its prompt across multiple evaluation criteria simultaneously. Textual gradient methods automate this for a single judge criterion, however they produce natural-language critiques, not numerical vectors. Thus, the conflict-resolution toolkit of multi-task learning (PCGrad, MGDA) does not apply to this multi-objective textual gradient setting. We extend TextGrad to the multi-objective setting and test four decomposition modes of textual gradient optimizers by varying how much cross-objective information the loss, gradient and optimizer LLMs share. We find the gradient's task-focus drops by 59% (9.0 to 3.7 out of 10) when the gradient LLM must provide feedback on multiple criteria jointly. Separately, we observe that naively combining single-objective optimized instructions into a single prompt degrades Spearman rho from 0.305 to 0.220 (-0.085). These results identify two separable failure modes: optimization-time gradient dilution and inference-time instruction interference, which together constrain the design space for multi-objective judge optimization using textual feedback.
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.