Applications have transitioned from monolithic to complex, cloud-native architectures, rendering traditional security testing methods obsolete. To keep up, Dynamic Application Security Testing (DAST) must evolve by revisiting the core fundamentals of black box testing: state, payloads, and assertions. Historically, application states were URL-driven, making it simpler to identify vulnerabilities, but modern architectures use actions and client-side changes that obscure state and technology stack. As payloads now often traverse multiple components, context-aware strategies are required to ensure they work across different systems. The need for modern black box testing to adapt is highlighted by the challenges of hidden tech stacks, delayed payload triggers, and noisy system behaviors, as seen in examples like the Log4j vulnerability. Detectify's approach includes innovations such as Dynamic Payload Rotation, which leverages machine learning to adaptively refine testing methods, ensuring they evolve alongside the applications they aim to protect.