In recent years, the flipped classroom has become prevalent in many educational settings. Flipped classroom adopts a pedagogical model in which short video lectures are viewed by students at home before class so that the teacher can lead students to participate in activities, problem-solving, and discussions. Yet the design or use of technology that employs planned instructional strategies with sustainable support of self-regulation is scant. We propose a technology-enhanced flipped language learning system (Flip2Learn) that provides facilitation and guidance for learning performance and self-regulation. A quasi-experimental study was carried out to examine whether Flip2Learn could enhance college students' self-regulatory skills and later contribute to the learning performance in the flipped classrooms. The results showed that Flip2Learn not only better prepared students for flipped classrooms but also better promoted learning performance compared to the conventional flipped classrooms. The results of this research advanced our understanding of the dynamics of flipped classrooms and represented a revolutionary new approach to the technology-enhanced learning for flipped classrooms.