We’ll explore the reality that no matter how carefully software is designed, users will always find ways to break, bypass, or use it in ways that developers never anticipated. Through real-world stories from my own experience, I’ll highlight unexpected user behaviors, the lessons learned from them, and why it's crucial for developers to expect the unexpected. Whether it's circumventing validation rules or using features in unintended ways, this presentation will challenge assumptions and provide insights on building more resilient and user-centric applications.