BACKGROUND: Workplace-Based Assessment (WPBA) has been widely utilized for assessing performance in training sites for both formative and summative purposes. Currently, with the recently updated duration of the family medicine (FM) training program in Saudi Arabia from four years to three years, the possible impact of such a change on assessment would need to be investigated. This objective was to explore the experiences of FM residents regarding the usage of WPBA as an assessment tool for improving clinical teaching at King Abdulaziz Hospital (KAH), Al Ahsa, Saudi Arabia. METHODS: The study involves an exploratory qualitative phenomenological approach targeting family medicine resident in KAH was used. Purposive sampling techniques were used. In this descriptive study, data was collected through the utilization of 1:1 semi-structured interviews guided by directive prompts. All recorded interviews were transcribed verbatim. An inductive analytical approach was applied for thematic analysis of transcripts. RESULTS: Fifteen participants were individually interviewed until data saturation was reached. The themes that emerged were organized into the categories of underlying principles of WPBA, the impact of the learning environment, associated opportunities and challenges, and making WPBA more effective. Participants expressed that the orientation provided by the program was insufficient, although the core principles were clear to them. They valued the senior peers' support and encouragement for the creation of a positive learning environment. However, time limit, workload, and a lack of optimum ideal implementation reduced the educational value and effectiveness of WPBA among senior residents. CONCLUSION: The study examined residents' experiences with WPBA and concluded that low levels of satisfaction were attributed to implementation-related problems. Improvements should be made primarily in two areas: better use of available resources and more systematic prior planning. Revision and assignment of the selection process were suggested, in addition to the implementation of the new curriculum. The research will assist stakeholders in selecting and carrying out evaluation techniques that will enhance residents' abilities.