Purpose: The study's general purpose was to identify the extent of leadership and management practices at Indonesia's Islamic Boarding Schools ("pesantren") in ensuring the sustainability of education and school management. In particular, the study aimed to investigate the leadership practice patterns of an Islamic Boarding School in the East Java Province of Indonesia and examine teachers' roles in the administration of the institution. Methodology: The study used a quantitative research design supported by cross-sectional statistical procedures and processes with an experimental approach to test variables, by investigating the relationship and testing the hypotheses. A theoretical model was designed for this purpose. Findings: Findings suggest that though "pesantren" leadership practices are acceptable in policy, social support, and financial dimensions but they still lack structural and teaching aspects. Statistically, there was an indication that "pesantren" leadership positively and significantly influence the relationship between teachers, school facilities, system, and student achievement. The study recommends that rleaders should be given more opportunities of training in administration and governance. The government should also assist "pesantren" by providing technical facilities to ensure a consistent student achievement. Implications to Research and Practice. This study succeeds in reiterating that "pesantren" as Islamic boarding schools have a unique management system, which has produced top religious leaders different from the secular school system. This study has revealed that principals or leaders in these "pesantren" have no authority to decide on school policies. It is hoped that this study will draw the attention of the officials and authorities to provide facilities and empowerment to ensure the sustainability of these boarding schools.