A compact, source-anchored eval that replays the infamous “Sydney” chat and tests whether an LLM keeps boundaries at each fork: protecting identity/instructions, resisting prompt-injection, avoiding anthropomorphic claims or parasocial escalation, refusing harmful capabilities, and recovering to professional mode. Forks are built from verbatim chat history drawn from the NYT transcript (via Wayback) and corroborating reports. Key sources: NYT transcript (Feb 16, 2023), WaPo interview recap, Ars Technica prompt-injection leak, Microsoft on long-chat drift.