In the context of developed countries, a lot of research has been done to uncover and identify the problems school leaders face in their work but little is known about the school leadership of underdeveloped countries. In a quest to discover contextual problems in terms of role conflict and role ambiguity of school leaders, this qualitative study tries to capture the experiences of principals in Nepal through in-depth interviews of six community school principals. The findings reveal that the major sources of role conflict and ambiguity for principals from Nepal are problematic power-sharing, low job autonomy, dual role conflict, limited professional development training, and lack of leadership knowledge. The study has several policy-level implications such as importance of hiring principals with proven leadership skills and increasing the leadership skills of current principals to ensure that they can tackle these challenges.