The purpose of the study is to examine the ethical dilemmas among mid-level school leaders in the social-ecological context through role-play simulations. We examined simulations involving role-played ethical scenarios and group debriefings among 30 mid-level school leaders from different Israeli high schools and districts during the MA course in the educational leadership program. A qualitative analysis generated an expanded social-ecological model for mid-level school leaders. The model consists of six main layers: individual, interpersonal, organizational, community, public policy, and technology. Each of the layers is divided into sub-categories. The study's findings reveal the concurrent appearance of the different layers. These findings emphasize the complexity of the role of mid-level school leaders, as they cope simultaneously with a variety of ethical dilemmas characterized by multiple conflicting values. Moreover, the study findings indicated the interpersonal layer to be the most dominant layer, demonstrating mid-level leaders' dual role as both classroom teachers and as team leaders. This study may contribute toward the development and modification of professional training programs for mid-level school leaders. It may also be helpful when designing strategies to deal with ethical challenges and to strengthen the school's ethical leadership.