Deepfakes - manipulated or forged audio and video media - pose significant security risks to individuals, organizations, and society at large. To address these challenges, machine learning-based classifiers are commonly employed to detect deepfake content. In this paper, we assess the robustness of such classifiers through a systematic penetration testing methodology, which we introduce as DeePen. Our approach operates without prior knowledge of or access to the target deepfake detection models. Instead, it leverages a set of carefully selected signal processing modifications - referred to as attacks - to evaluate model vulnerabilities. Using DeePen, we analyze both real-world production systems and publicly available academic model checkpoints, demonstrating that all tested systems exhibit weaknesses and can be reliably deceived by simple manipulations such as time-stretching or echo addition. Furthermore, our findings reveal that while some attacks can be mitigated by retraining detection systems with knowledge of the specific attack, others remain persistently effective. We release all associated code.