Personal learning environments (PLEs) offer valuable opportunities to enhance overall learning experiences while nurturing technological and learning skills of contemporary learners. To maximize these opportunities researchers and practitioners must clearly understand how learners’ digital literacy (DL) and self-regulated learning (SRL) skills are interrelated within PLEs. This paper presents the quantitative findings of an ongoing longitudinal mixed methods study designed to identify and describe these relationships. Structural equation modeling is used to test competing two-wave panel models using online survey data from 181 participants. The results support the acceptance of a model with significant positive reciprocal relationships between DL component constructs and the SRL construct. We contribute, via empirical evidence, to clarifying the direction and extent to which DL and SRL skills of undergraduates influence each other within PLEs. The paper concludes with a discussion of the implications for theory and practice together with future research opportunities.