As digital transformation pedagogy, electronic portfolio (ePortfolio) projects embody experiential assessment practices that are fair, inclusive, and authentic. These projects, a substrate for knowledge acquisition, knowledge production, and knowledge mobilization, become a driving force toward task completion and subsequent mastery of language skills. Learning mediated by ePortfolio technology espouses cognition (my thinking), affect (my feeling), and conation (my doing)—domains that undergird self-regulation in technology-mediated language learning environments. Empirical evidence of intermediate-level learners of English as a second language (ESL) and their capstone ePortfolio projects over five semesters show that students engage in meaningful learning and reflection once cognition, affect, and conation work in tandem. Throughout the ePortfolio development process, students relied on a mutual interaction of systems to articulate—in speech and writing—how they performed certain tasks as well as to explicate why they had completed them in a certain way– an ecological approach to constructivism. These experiences of ESL learners may help inform the field of technology-mediated language learning, teaching, and assessment; contribute toward a better understanding of ePortfolio pedagogy; and stimulate discussions on contemporary theories of learning that align with an authentic form of assessment in blended and online language learning spaces.