Large language models are increasingly deployed in user-facing products that handle sensitive personal data while interacting with untrusted external content. This makes them a prime target for prompt injection attacks, in which an adversary injects malicious instructions in that content to hijack the model. Fine-tuning-based defenses have been proposed to mitigate these attacks by training models to follow benign user instructions and ignore injected ones. Lacking formal guarantees, these defenses are evaluated empirically against the most effective realistic attacks available at the time, often reporting near-zero attack success rates -- giving developers, and the users who depend on them, a false sense of security and leaving open the possibility that future, more capable attacks could circumvent them and cause severe consequences in widely deployed systems. In this paper, we argue that developers should stress-test their defenses before release, and we introduce an auditing framework that does so without requiring defenders to invent the next state-of-the-art attack. Our key insight is that the fine-tuning process itself yields useful artifacts: intermediate checkpoints that serve as stepping stones for optimization-based attacks. Although these artifacts are unavailable to real attackers, we show that the vulnerabilities they expose are genuine and can be exploited by realistic adversaries. Instantiating our framework with optimization-based attacks such as GCG and BEAST, we raise attack success rates against state-of-the-art defenses from near zero to as high as 96\%, revealing weaknesses missed by prior evaluations. Our results show that current evaluation practices can substantially overestimate robustness, and that auditing defenses under strong adversaries before deployment shortens the feedback loop and helps prevent attacks from causing real-world harm to users.

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