Effective discharge education is personalized: a clinician adapts the discharge plan to each patient's literacy, recall, and personality. Before large language models (LLMs) take on this role with real patients, they need to be evaluated in conversations with diverse patients, yet existing evaluations target static, artifact-generation, or question-answering tasks. We introduce **DischargeBench**, a pre-deployment benchmark in which a candidate LLM educator teaches a persona-grounded simulated patient in an open-ended, multi-turn conversation. We curate **MIMIC-IV-Ext-DischargeBench**, 320 cases across 16 ICD chapters, each paired with a patient persona that varies personality, education level, health literacy, and recall. Each conversation is scored on Conversation Quality, Topic Checklist Score (TCS), Simulated Comprehension Score (SCS), and a Claim-Level Safety Audit (CLSA) by an LLM judge validated against physician annotations. Across eight closed- and open-source LLMs, the best model scored only 0.70 on TCS and 0.72 on SCS, and distrustful and anxious patients lowered comprehension for every model. DischargeBench is intended as a screening step before human evaluation, not as evidence of readiness to educate patients.

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