This special issue of the Journal of Educational Supervision, Cases in Critical Supervision within School Contexts, critically examines educational supervision models, highlighting their limitations in fostering equity and inclusivity. As greater attention and awareness of diverse identities and experiences becomes more common in schools there also needs to be acknowledgement of how supervision is experienced by educators and enacted by instructional supervisors. We argue for a paradigm shift towards more empathetic and diverse supervisory practices that consider the varied backgrounds and needs of students. Throughout this special issue, researchers propose innovative approaches that prioritize collaboration, understanding, and the recognition of the unique potential of every teacher, educator, and student. Empowered with a willingness and an awareness of how educational experiences can be experienced differently, researchers suggest supervisory models to transform educational environments into spaces where all students, especially those from marginalized groups, can thrive.