PurposeTo evaluate the implementation of a longitudinal assessment framework utilizing entrustable professional activities (EPAs) in dental education during the initial 2‐year implementation.MethodThe Consolidated Framework for Implementation Research was utilized to evaluate contextual factors influencing implementation across the following domains: innovation, outer setting, inner setting, individuals, and process. Purposive sampling was used to ascertain a diverse pool of participants and various perspectives. Inclusion criteria required engagement for >12 months at the time of the study. A semi‐structured interview guide was developed. Two focus groups of faculty and staff and four individual leadership interviews were conducted via Microsoft Teams, transcribed, and thematic analyses were performed using MAXQDA.ResultsFifteen participants described innovation design details, adaptability, complexity, and relative advantage. The contextual fabric of the setting was evaluated, highlighting the influence of the pandemic, institutional culture, structural shifts, and the pivotal role played by champions. The implementation process was investigated with a focus on training, engagement, access to information, faculty capability, motivation, learner experience, and continual assessment of implementation processes. Data suggests the framework was multi‐dimensional, evolving, and learner‐centered. It facilitated early identification of learners requiring support, provided comprehensive information guiding entrustment and practice readiness decisions and demonstrated preliminary evidence of effectiveness of the innovation.ConclusionEngaging in longitudinal assessment using EPAs is multifaceted and influenced by implementation context and intrinsic motivation prevalent among faculty members. The study identifies areas for refinement in support of continuous quality improvement and implementation of this innovative assessment framework in dental education, including technological support, training, and ongoing alignment.