Stop Testing Attacks, Start Diagnosing Defenses: The Four-Checkpoint Framework Reveals Where LLM Safety Breaks

Abstract: LLMs deploy safety mechanisms to prevent harmful outputs, yet these defenses remain vulnerable to adversarial prompts. While existing research demonstrates that jailbreak attacks succeed, it does not explain \textit{where} defenses fail or \textit{why}. To address this gap, we propose that LLM safety operates as a sequential pipeline with distinct checkpoints. We introduce the \textbf{Four-Checkpoint Framework}, which organizes safety mechanisms along two dimensions: processing stage (input vs.\ output) and detection level (literal vs.\ intent). This creates four checkpoints, CP1 through CP4, each representing a defensive layer that can be independently evaluated. We design 13 evasion techniques, each targeting a specific checkpoint, enabling controlled testing of individual defensive layers. Using this framework, we evaluate GPT-5, Claude Sonnet 4, and Gemini 2.5 Pro across 3,312 single-turn, black-box test cases. We employ an LLM-as-judge approach for response classification and introduce Weighted Attack Success Rate (WASR), a severity-adjusted metric that captures partial information leakage overlooked by binary evaluation. Our evaluation reveals clear patterns. Traditional Binary ASR reports 22.6\% attack success. However, WASR reveals 52.7\%, a 2.3$\times$ higher vulnerability. Output-stage defenses (CP3, CP4) prove weakest at 72--79\% WASR, while input-literal defenses (CP1) are strongest at 13\% WASR. Claude achieves the strongest safety (42.8\% WASR), followed by GPT-5 (55.9\%) and Gemini (59.5\%). These findings suggest that current defenses are strongest at input-literal checkpoints but remain vulnerable to intent-level manipulation and output-stage techniques. The Four-Checkpoint Framework provides a structured approach for identifying and addressing safety vulnerabilities in deployed systems.