Self-regulated learning (SRL) is associated with university student academic success outcomes, however students often need support to develop these skills. Technology-mediated feedback is one strategy that may aid educators in supporting students’ SRL development. This study aims to explore whether a technology-mediated feedback strategy targeting tutorial preparation for flipped classrooms enhances first-year students’ self-report SRL and observed implementation of the strategy. Self-report SRL was measured using the Motivated Strategies for Learning Questionnaire (MSLQ); strategy implementation profiles were based on lecture video access patterns. First-year psychology students (n = 99) were sent technology-mediated feedback emails aimed at developing their SRL. Paired-samples t-tests revealed significant increases in post-intervention self-reported motivational SRL subscales; self-reported and observed learning strategies implementation did not improve. Future research could build upon this exploratory work to form a multi-pronged strategy to increase understanding of the role of technology-mediated feedback in first-year students’ SRL development for flipped classroom learning.