In this study, researchers designed and implemented a 1-year professional development (PD) program that focused on supporting teachers in evaluating and selecting digital learning contents. Participants in this investigation included 109 teachers who consented to the study amongst a total of 171 teachers from ﬁve school districts across central Ohio. In addition to their participation in the PD program, they completed surveys, interviews, and self-reﬂections in this mixed-method study. The results revealed that teachers’ perceived TPACK increased over time throughout the PD program, suggesting that training teachers to evaluate digital contents can be an effective PD model to improve teachers’ capacity in learning technology integration. The PD program was especially effective for teachers with less prior experience in technology integration or related training. Mathematics teachers, in comparison to teachers from other disciplines, began with low TPACK; however, these initial differences gradually diminished over the course of the PD program. In terms of their motivation in digital content evaluation, teachers’ expectancy for success increased signiﬁcantly while their task values remained medium high. The qualitative analyses provided additional insights and revealed design suggestions for success in future PDs.