Some nurses are responding rebelliously to the changing healthcare landscape by challenging the status quo and deviating from suboptimal practices, professional norms, and organizational rules. While some view rebel nurse leadership as challenging traditional structures to improve patient care, others see it as disruptive and harmful. These diverging opinions create dilemmas for nurses and nurse managers in daily practice. To understand the context, dilemmas, and interactions in rebel nurse leadership, we conducted a multiple case study in two Dutch hospitals. We delved into the mundane practices to expand the concept of leadership-as-practice. By shadowing rebel nurse practices, we identified three typical leadership practices which present the most common “lived” experiences and dilemmas of nurses and nurse managers. Overall, we noticed that deviating acts were more often quick fixes rather than sustainable changes. Our research points to what is needed to change the status quo in a sustainable manner. To change unworkable practices, nurses need to share their experienced dilemmas with their managers. In addition, nurse managers must build relationships with other nurses, value different perspectives, and support experimenting to promote collective learning.