Against the background of the rapid development of digital technology, the integration of technology in the field of education has become an inevitable trend, and middle school Chinese classroom teaching has also ushered in an important opportunity for model innovation. Technology empowerment has injected new vitality into middle school Chinese teaching, promoting the formation of various new teaching models such as contextualized teaching, personalized learning, and interactive discussion, which have effectively expanded the boundaries and dimensions of Chinese teaching. However, in the practice process, middle school Chinese teaching under technology empowerment also faces many dilemmas, such as insufficient adaptability between technology application and the essence of Chinese teaching, an imbalance between teachers’ technical literacy and teaching needs, scattered students’ learning attention, and homogenization of teaching resources. This paper deeply explores the new models of middle school Chinese classroom teaching under technology empowerment, analyzes the dilemmas encountered in practice, and puts forward corresponding countermeasures, aiming to provide a useful reference for promoting the in-depth integration of technology and middle school Chinese teaching.