Assessments are integral and ingrained with learning. Traditional assessments have mainly focused on the student’s ability to acquire the cognitive component of learning outcomes. However, with the development of concepts of learning, the notion of assessment is also changing, with attention directed to include affective and psychomotor domains. While the cognitive component of learning can be acquired within educational settings or via other flexible educational resources, learning related to affective and psychomotor domains is best undertaken in real-life settings. The actual skills and experiences gained through real-life settings enable the student solve problems they encounter later in the real world. Furthermore, cumulative real-life learning experiences influence student’s attitudes toward learning and assessments. Clinical competence by the student has received special attention in dental education. Clinical competence encompasses one’s ability to integrate knowledge, skills, attitudes, and values into a given clinical situation, so that the patient receives the best possible care in a safe environment. Therefore, the modern dental curricula also/equally emphasize the psychomotor and affective domains, where clinical and practical skills acquisition is given more weighting. Thus, the assessments designed for the latter years of dentistry training largely focus on clinical competencies and the ability of the student in applying knowledge and skills into real-life clinical practices. Assessment of a dental student’s overall clinical competence is a mandatory requirement before considering for licensing to practice dentistry. Unlike the knowledge component, assessment of skills, skills application, attitudes, and values need to be assessed through a structured approach in an integrated manner. Against this backdrop, workplace-based assessments (WPBAs) have been proposed and accepted as useful methods/tools of assessment in dentistry. At the same time, WPBAs facilitate further learning of a student through feedback following assessments. WPBAs may include a range of formative or summative assessments, explicitly targeted at specific competencies. In dental educational settings, WPBAs are conducted in the form of case-based discussions, mini-clinical evaluation exercises, and direct observation of procedural skills. Similarly, portfolio is another useful tool of formative assessments. Since portfolio facilitates reflective learning, it has been popularly implemented in the dental health training institutes. A critical reflection of both positive and negative experiences gathered at the real workplace helps students improve their future learning and progression as clinical practitioners.