Superintendency is regarded as one of the most visible and powerful leadership roles in the world of education today (Sovine, 2000). This research was conducted to identify the challenges faced by assistant superintendents and their perspectives in terms of preparation and support. The study made use of the qualitative research design and was conducted in Region III, Philippines with 10 participants. Findings showed that assistant superintendents faced issues and challenges in terms of organizational and job-related mandates and have negative perspectives about the preparation and support extended to them. During the day-to-day operations in their respective divisions, assistant superintendents face governance and culture-related problems in terms of procurement, handling administrative cases and managing personnel-related actions. On the other hand, during the epidemic, public school superintendents faced several hurdles due to the complexities and challenges of education reforms at both the national and local levels. The school systems are undergoing continuous reforms and redirections as they transition from distance learning to limited face-to-face instructions. Additional obstacles have arisen because of increased public pressure for higher student performance in the face of the pandemic, causing problems throughout the educational system. As educational leaders, the Assistant Superintendents have a lot of work to accomplish to fulfill their duties. Furthermore, in the new normal, there is a leadership crisis due to teacher shortages, insufficient school finance, a lack of school facilities and resources to manage distance education, and excessive time demands. These complicated elements have added to the difficulties that assistant superintendents have in meeting the demands of their jobs. Finally, the critical requirement for skills and competencies to deliver efficiently and effectively has caused them stress, prompting them to seek personal and professional help by whatever means available. Based on the findings and analysis generated, this study recommends several pre-service activities, programs, and projects relevant to superintendency preparation and support. Conduct of immersion programs to prepare aspiring superintendents; coaching and mentoring of skills and competencies relevant to the functions of the job; attend graduate school; participate in exchange study programs; undergo induction program provided by DepEd; and intense preparation on legal and moral aspects of the leadership role.