Document parsing and recognition are fundamental capabilities for vision-language models (VLMs) and document processing systems. However, existing Optical Character Recognition (OCR) and document parsing benchmarks are increasingly limited in coverage and difficulty: many focus on common document genres or uniformly sampled pages where modern parsers already perform strongly, while offering limited annotation for expert-domain structures such as chemical formula, music notation, complex tables, and cross-page layouts. We introduce Dr. DocBench, a difficulty-aware benchmark for expert-level document parsing. Built from a large-scale multilingual book corpus, Dr. DocBench spans 52 BISAC subject domains and selects challenging documents through parser-failure-based sampling, targeting cases where multiple state-of-the-art systems struggle. It contains 4,514 annotated pages from long documents averaging around 100 pages, with 65k high-quality page- and block-level annotations for layout, reading order, hierarchical relations, and domain-specific visual contents. Evaluations of pipeline-based parsers and general-purpose VLMs show that strong performance on existing benchmarks does not transfer to our expert-level document parsing. Our analysis reveals substantial failures across subjects, content types, and structural attributes, highlighting Dr. DocBench as a comprehensive testbed for diagnosing and advancing document intelligence.