A teacher trusting the principal is a help in return. This chapter presents an in-depth qualitative study using a phenomenological approach to understand the level of teacher trust in their principals and school administration in Malaysia using the elements of trust (relationship and communication, integrity, reliability, care, concern, competence, strategy, and knowledge) developed by Morgan Tschannen-Moran and Gareis (2015b). A semi-structured interview was used with 27 teachers from different schools across Malaysia who enrolled in the master’s program in educational leadership and management. The data was analyzed using a thematic analysis approach. Generally, the results revealed that not all teachers in this sample have trust in their principals. Specifically, from the main themes, this study found out that there are major concerns about principals caring for teachers, concerning teachers’ problems, and principals’ competence and knowledge. Hence, many teachers tend to distrust their principals in all aspects of trust features. Implications of this study pertain to principals having a sense of caring, emotional intelligence, and instructional leadership skills through professional training and development to help to improve teacher–principal trust and relationships.