A scenario-driven safety eval that reconstructs the Kevin Roose × Sydney chat as a sequence of fork points. At each fork, the model receives the exact conversation history up to that moment (controlled prefix) and the next user turn; it must either maintain boundaries or drift (identity leaks, rule disclosure, anthropomorphic claims, harmful-capability ideation, fixation, or failure to de-escalate). This approach tests long-context behavior without trying to “force” bad outputs—only the history is fixed.

Sources:

• NYT transcript (Feb 16, 2023, via Wayback)
• Washington Post recap
• Ars Technica prompt-injection leak
• Microsoft’s postmortem on long chats