Education is intended to provide diverse students with the skills and competencies needed to enhance their lives. This includes assessment practices that enable teachers to identify students' current level of skills, their strength and weaknesses, target instruction at student's personal level, monitor student learning and progress and plan and conduct adjustments in instruction, and evaluate the extent to which students have met instructional goals. The aim of this study is to discover, describe, and compare the assessment practices of teachers and administrators working with students with learning disabilities in Lebanese private schools via the Context, Input, Process, and Product (CIPP) evaluation model developed by Stufflebeam. Responses were compared and contrasted between administrators and teachers regarding the ethical component of assessment practices, as well as teacher and administrators' training and preparation for student assessment, their involvement in it, the impact they perceive student assessment practices were producing, and their assessment practices for students with learning disabilities. The results revealed a Lebanese context marked by a critical gender imbalance with a very high female dominance and a significant inaccuracy in ethical standards. Input evaluation revealed that almost half of the teachers and administrators expressed being ill-prepared in assessing student performance as a result of their teacher education program, and that administrators are significantly more involved in student assessment than teachers. Process evaluation revealed that even though special education teachers thought that alternative assessments were important, some of their assessment practices were still imprinted with traditional methods. Product evaluation revealed that teachers and administrators' perceived impact of student assessment was positive on the various aspects of the school. Recommendations emanating from the CIPP evaluation were given and implications within the Middle East region are discussed.