The purpose of this study is to determine the challenges school principals facing in the context of technology leadership. This is a qualitative case study guided by the National Educational Technology Standards for Administrators (NETS*A). Six elementary school principals working in a large city in southeastern Turkey participated into the study. The data were collected through face-to-face interviews via a semi-structured interview protocol. The data collection tool was developed through pilot studies based on expert opinions. The data were analyzed through a thematic approach and validity and reliability were investigated via peer-review, member checking, and inter-coder reliability processes. The findings show that in assuming their roles as technology leaders school principals face various challenges, including bureaucracy, lack of resources, resistance to innovation, lack of in-service training, and poverty. Based on the findings, various measures are recommended to diminish bureaucratic obstacles and organize sustainable in-service training activities in order to overcome the challenges that school principals are facing in the context of technology leadership.