Purpose To investigate knowledge and image interpretation skill development in residency by studying scores on knowledge and image questions on radiology tests, mediated by the training environment. Materials and Methods Ethical approval for the study was obtained from the ethical review board of the Netherlands Association for Medical Education. Longitudinal test data of 577 of 2884 radiology residents who took semiannual progress tests during 5 years were retrospectively analyzed by using a nonlinear mixed-effects model taking training length as input variable. Tests included nonimage and image questions that assessed knowledge and image interpretation skill. Hypothesized predictors were hospital type (academic or nonacademic), training hospital, enrollment age, sex, and test date. Results Scores showed a curvilinear growth during residency. Image scores increased faster during the first 3 years of residency and reached a higher maximum than knowledge scores (55.8% vs 45.1%). The slope of image score development versus knowledge question scores of 1st-year residents was 16.8% versus 12.4%, respectively. Training hospital environment appeared to be an important predictor in both knowledge and image interpretation skill development (maximum score difference between training hospitals was 23.2%; P < .001). Conclusion Expertise developed rapidly in the initial years of radiology residency and leveled off in the 3rd and 4th training year. The shape of the curve was mainly influenced by the specific training hospital. © RSNA, 2017 Online supplemental material is available for this article.