Background: With medical education shifting towards student-centered models, medical students are expected to be self-regulated learners. Advancement in technologies has been suggested to be supportive of students’ self-regulated learning (SRL). There is an urgent need to understand what factors contributed to students’ self-initiated technology use, and how does students’ technology use influence their SRL. Method: This study took place in a midwestern university medical school, which implements a flipped classroom model where students are required to learn independently all the course materials before class. Twenty-six first- and second-year medical students participated in a semi-structured interview about their self-initiated technology use, contributing factors towards technology use, and SRL strategies they adopt in learning. A qualitative description methodology using thematic analysis was used to identify key themes from the interview data. Results: Medical students reported the use of four types of technologies for learning: video resources (supporting rehearsal, elaboration and planning), review resources (supporting rehearsal, effort control, and self-assessment), management tools (supporting organization, elaboration, goal-setting, and time management), and social media (supporting help-seeking and effort regulation). Three key determinants of students’ self-initiated technology use were identified, which were: perceived usefulness, subjective norms, and educational compatibility. Conclusions: By probing medical students’ self-initiated technology use, SRL strategies, and determinants of technology use, this study suggested that in self-directed learning environment, medical students used a variety of third-party resources to facilitate learning and develop necessary learning strategies. This study also provided important implications for medical educators and instructional designers to better support students’ effective use of technologies for learning.