Prompts in the Wild: A Large Analyzed Collection of Transactional Prompts in Code

Large language models (LLMs) are widely used for open-ended tasks, but underspecified prompts can lead to low-quality answers and additional interaction. This paper studies whether structured prompt design improves response quality while reducing user effort. We compare three prompt conditions: a raw prompt, a checklist-improved prompt, and a clarifying-question prompt. We evaluate these conditions across four task types--summarization, planning, explanation, and coding--using three LLM systems: ChatGPT, Claude, and Grok. Each output is scored with a unified rubric covering task completion, correctness, compliance, and clarity. Checklist-improved prompts achieved the highest mean rubric score, 7.50 out of 8, compared with 5.67 for raw prompts and 6.67 for clarifying-question prompts. Checklist prompts also produced the best quality-effort tradeoff, using fewer average tokens than both raw and clarifying prompts. These results suggest that a simple prompt checklist can improve LLM responses while reducing unnecessary interaction.

Large language models are highly sensitive to prompts, but this sensitivity is usually studied through task-relevant instructions, demonstrations, or reasoning cues. In this paper, we study a different form of prompt sensitivity: whether prompts that are semantically unrelated to the task can nevertheless steer model behavior. We call them spurious prompts and show their surprising efficacy. We also propose a simple black-box search procedure for discovering them. Across reasoning and question-answering benchmarks, using models ranging from 0.8B to 27B parameters and spanning three model families, we show that spurious prompts can improve performance, often matching or outperforming standard prompting baselines and task-aware prompt optimization. We further show that they can steer models toward unintended behaviors, such as repeatedly selecting the first answer option, producing incorrect answers, returning an even, prime or small number without explicitly instructing the model to do so. These findings reveal a new kind of prompt sensitivity: LLMs can be systematically steered by prompts that are unrelated to the task they are asked to solve. Our code is available at https://github.com/Batorskq/spurious

In this paper, we define the quantity of prompting complexity: for a fixed instruction-tuned language model, what is the shortest plausible prompt that makes deterministic decoding produce a target text? It is an LM-relative analogue of resource-bounded Kolmogorov complexity: the prompt is a program, the model interface is the interpreter, and information omitted from the prompt is supplied by the model's weights, training distribution, tokenizer, template, and decoding rule. Unlike classical Kolmogorov complexity, this measure is intentionally non-universal. In the finite-context setting it is computable by enumeration, but there is no model-independent invariance theorem; the same text may be cheap for one model and inaccessible or expensive for another. To keep the search space aligned with prompt engineering, we restrict programs to plausible human-readable texts rather than arbitrary token strings. We extend the exact definition to soft prompting complexity for approximate outputs, yielding a lossy notion of model-relative text compression and a formal target for prompt optimization. We also define prompting distance by comparing shortest generating prompts, and behavioral prompting complexity for reaching any output satisfying a specification. Based on these formulations, we define a research agenda for empirically studying which texts and behaviors are accessible from short plausible prompts under a fixed LM interface.