While vision-language models (VLMs) have advanced into detailed image description, evaluation remains a challenge. Standard metrics (e.g. CIDEr, SPICE) were designed for short texts and tuned to recognize errors that are now uncommon, such as object misidentification. In contrast, long texts require sensitivity to attribute and relation attachments and scores that localize errors to particular text spans. In this work, we introduce PoSh, a metric for detailed image description that uses scene graphs as structured rubrics to guide LLMs-as-a-Judge, producing aggregate scores grounded in fine-grained errors (e.g. mistakes in compositional understanding). PoSh is replicable, interpretable and a better proxy for human raters than existing metrics (including GPT4o-as-a-Judge). To validate PoSh, we introduce a challenging new dataset, DOCENT. This novel benchmark contains artwork, paired with expert-written references, and model-generated descriptions, augmented with granular and coarse judgments of their quality from art history students. Thus, DOCENT enables evaluating both detailed image description metrics and detailed image description itself in a challenging new domain. We show that PoSh achieves stronger correlations (+0.05 Spearman $ρ$) with the human judgments in DOCENT than the best open-weight alternatives, is robust to image type (using CapArena, an existing dataset of web imagery) and is a capable reward function, outperforming standard supervised fine-tuning. Then, using PoSh, we characterize the performance of open and closed models in describing the paintings, sketches and statues in DOCENT and find that foundation models struggle to achieve full, error-free coverage of images with rich scene dynamics, establishing a demanding new task to gauge VLM progress. Through both PoSh and DOCENT, we hope to enable advances in important areas such as assistive text generation.