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.

Understanding how developers interact with AI coding assistants requires more than chat logs or git histories in isolation; it requires reconstructing the full context: which prompt led to which edit, what the developer tried and discarded, and how their strategy evolved over time. We present RECAP (Replay and Examine Captured AI Programming), an open-source platform that (1) passively records AI chat sessions and fine-grained code edits inside VS Code without disrupting the developer’s workflow, (2) merges them into a unified timeline for interactive session replay, and (3) exposes an extensible analysis layer, with example modules for behavioral classification and AI reliance measurement. Deployed in a university software engineering course, RECAP captured 2,034 prompts and 8,239 code edits from 41 students across a multi-week project. We demonstrate how the platform’s linked data and replay capabilities enable analyses of developer-AI interaction patterns that no single data source could support.

In the era of Large Language Models (LLMs), establishing effective evaluation methods and standards for diverse human-AI interaction systems is increasingly challenging. To encourage more transparent documentation and facilitate discussion on human-AI system evaluation design options, we present an evaluation card SPHERE, which encompasses five key dimensions: 1) What is being evaluated?; 2) How is the evaluation conducted?; 3) Who is participating in the evaluation?; 4) When is evaluation conducted?; 5) How is evaluation validated? We conduct a review of 39 human-AI systems using SPHERE, outlining current evaluation practices and areas for improvement. We provide three recommendations for improving the validity and rigor of evaluation practices.