Pentesting is meant to uncover security weaknesses, but sometimes the process itself becomes an exercise in frustration. From unclear scopes and unresponsive clients to network misconfigurations and unexpected legal roadblocks, every pentester has war stories of engagements gone wrong. This talk dives into real-world pentesting pain points, sharing firsthand experiences of what makes assessments more difficult than they need to be—and how to avoid these pitfalls. Whether you’re a seasoned pentester, a blue teamer trying to prepare for a test, or a purple teamer bridging the gap, understanding these challenges can help ensure your next engagement is smoother and more effective. We’ll cover the most common mistakes from all sides of the table, such as poor scoping, lack of communication, ineffective remediation, and unrealistic expectations. Beyond just the horror stories, this session provides actionable lessons to help security teams and consultants work together more efficiently. Learn how to avoid common traps, improve collaboration, and turn painful experiences into opportunities for a more productive outcome.