Prompt underspecification is a common challenge when interacting with LLMs. In this paper, we present an in-depth analysis of this problem, showing that while LLMs can often infer unspecified requirements by default (41.1%), such behavior is fragile: Under-specified prompts are 2x as likely to regress across model or prompt changes, sometimes with accuracy drops exceeding 20%. This instability makes it difficult to reliably build LLM applications. Moreover, simply specifying all requirements does not consistently help, as models have limited instruction-following ability and requirements can conflict. Standard prompt optimizers likewise provide little benefit. To address these issues, we propose requirements-aware prompt optimization mechanisms that improve performance by 4.8% on average over baselines. We further advocate for a systematic process of proactive requirements discovery, evaluation, and monitoring to better manage prompt underspecification in practice.

Current model testing work has mostly focused on creating test cases. Identifying what to test is a step that is largely ignored and poorly supported. We propose Weaver, an interactive tool that supports requirements elicitation for guiding model testing. Weaver uses large language models to generate knowledge bases and recommends concepts from them interactively, allowing testers to elicit requirements for further testing. Weaver provides rich external knowledge to testers and encourages testers to systematically explore diverse concepts beyond their own biases. In a user study, we show that both NLP experts and non-experts identified more, as well as more diverse concepts worth testing when using Weaver. Collectively, they found more than 200 failing test cases for stance detection with zero-shot ChatGPT. Our case studies further show that Weaver can help practitioners test models in real-world settings, where developers define more nuanced application scenarios (e.g., code understanding and transcript summarization) using LLMs.