Objectives: Planning and evaluation are highly interrelated in the cycle of ongoing improvements in dental specialization programs. The aim of this study is to look at the Saudi Board of Endodontics (SBE) program to see if it might benefit from applying an evaluation framework specifying processes and outcomes, identifying measures, and developing an appropriate description for the program. Methods: Stufflbeam’s context, inputs, process and product (CIPP) evaluation model, a management-oriented approach, was applied. Results: The CIPP model indicates what may be key components for assessing the processes and contents of the program under study, and for making pedagogical improvements. The framework consists of a program’s rationale, evaluation questions, codes of behavior, evaluation models, and possible issues for evaluation. Conclusion: The systematic use of the CIPP evaluation framework highlights a number of challenges that may put the sustainability of programs at risk. It also provides suggestions to overcome any ongoing issues accompanying the process of implementation. Utilizing such versatile models may be of benefit to similar training programs, and should be considered by policymakers.