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Main Authors: Bhuiya, Neeladri, Dasgupta, Shib Sankar, McCallum, Andrew, Chang, Haw-Shiuan
Format: Preprint
Published: 2026
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Online Access:https://arxiv.org/abs/2603.21438
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author Bhuiya, Neeladri
Dasgupta, Shib Sankar
McCallum, Andrew
Chang, Haw-Shiuan
author_facet Bhuiya, Neeladri
Dasgupta, Shib Sankar
McCallum, Andrew
Chang, Haw-Shiuan
contents To discover the weaknesses of LLMs, researchers often embed prompts into a vector space and cluster them to extract insightful patterns. However, vector embeddings primarily capture topical similarity. As a result, prompts that share a topic but differ in specificity, and consequently in difficulty, are often represented similarly, making fine-grained weakness analysis difficult. To address this limitation, we propose PROMPT2BOX, which embeds prompts into a box embedding space using a trained encoder. The encoder, trained on existing and synthesized datasets, outputs box embeddings that capture not only semantic similarity but also specificity relations between prompts (e.g., "writing an adventure story" is more specific than "writing a story"). We further develop a novel dimension reduction technique for box embeddings to facilitate dataset visualization and comparison. Our experiments demonstrate that box embeddings consistently capture prompt specificity better than vector baselines. On the downstream task of creating hierarchical clustering trees for 17 LLMs from the UltraFeedback dataset, PROMPT2BOX can identify 8.9\% more LLM weaknesses than vector baselines and achieves an approximately 33\% stronger correlation between hierarchical depth and instruction specificity.
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publishDate 2026
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spellingShingle PROMPT2BOX: Uncovering Entailment Structure among LLM Prompts
Bhuiya, Neeladri
Dasgupta, Shib Sankar
McCallum, Andrew
Chang, Haw-Shiuan
Computation and Language
To discover the weaknesses of LLMs, researchers often embed prompts into a vector space and cluster them to extract insightful patterns. However, vector embeddings primarily capture topical similarity. As a result, prompts that share a topic but differ in specificity, and consequently in difficulty, are often represented similarly, making fine-grained weakness analysis difficult. To address this limitation, we propose PROMPT2BOX, which embeds prompts into a box embedding space using a trained encoder. The encoder, trained on existing and synthesized datasets, outputs box embeddings that capture not only semantic similarity but also specificity relations between prompts (e.g., "writing an adventure story" is more specific than "writing a story"). We further develop a novel dimension reduction technique for box embeddings to facilitate dataset visualization and comparison. Our experiments demonstrate that box embeddings consistently capture prompt specificity better than vector baselines. On the downstream task of creating hierarchical clustering trees for 17 LLMs from the UltraFeedback dataset, PROMPT2BOX can identify 8.9\% more LLM weaknesses than vector baselines and achieves an approximately 33\% stronger correlation between hierarchical depth and instruction specificity.
title PROMPT2BOX: Uncovering Entailment Structure among LLM Prompts
topic Computation and Language
url https://arxiv.org/abs/2603.21438