Abstract
Large language models (LLMs) have demonstrated several emergent behaviors with scale, including reasoning and fluency in long-form text generation. However, they continue to struggle with tasks requiring precise spatial and positional reasoning. ASCII art, a symbolic medium where characters encode structure and form, provides a unique probe of this limitation. We introduce ASCIIBench, a novel benchmark for evaluating both the generation and classification of ASCII-text images. ASCIIBench consists of a filtered dataset of 5,315 class-labeled ASCII images and is, to our knowledge, the first publicly available benchmark of its kind. Alongside the dataset, we release weights for a fine-tuned CLIP model adapted to capture ASCII structure, enabling the evaluation of LLM-generated ASCII art. Our analysis shows that cosine similarity over CLIP embeddings fails to separate most ASCII categories, yielding chance-level performance even for low-variance classes. In contrast, classes with high inte