Arguably, constructive alignment has been the major challenge for assessment in the context of problem-based learning (PBL). PBL focuses on promoting abilities such as clinical reasoning, team skills and metacognition. PBL also aims to foster self-directed learning and deep learning as opposed to rote learning. This has incentivized researchers in assessment to find possible solutions. Originally, these solutions were sought in developing the right instruments to measure these PBL-related skills. The search for these instruments has been accelerated by the emergence of competency-based education. With competency-based education assessment moved away from purely standardized testing, relying more heavily on professional judgment of complex skills. Valuable lessons have been learned that are directly relevant for assessment in PBL. Later, solutions were sought in the development of new assessment strategies, initially again with individual instruments such as progress testing, but later through a more holistic approach to the assessment program as a whole. Programmatic assessment is such an integral approach to assessment. It focuses on optimizing learning through assessment, while at the same gathering rich information that can be used for rigorous decision-making about learner progression. Programmatic assessment comes very close to achieving the desired constructive alignment with PBL, but its wide adoption--just like PBL--will take many years ahead of us.