Using the Technological Pedagogical Content Knowledge (TPACK) framework, this study investigated whether teachers’ technology integration practice and self-reported technological pedagogical content knowledge varied between different levels of teaching experience. We also explore some of the challenges of integrating technology into language teaching. Seventy-three pre-service and in-service teachers (mean age = 34) who had done graduate-level coursework participated in the study. The participants included teachers of English as a foreign language of various ethnic and teaching backgrounds. Some were native English speakers, some were not. Data were collected through a TPACK self-assessment survey that included open-ended questions. Overall, the analyses showed differences between novice and expert teachers in their understanding of pedagogical knowledge, technology knowledge, technological content knowledge, technological pedagogical knowledge, and technological pedagogical content knowledge. The two remaining subscales in the survey (pedagogical content knowledge and content knowledge) showed no difference in perceived knowledge between the novice and expert groups. In the qualitative data, four themes commonly emerged from the open-ended questions, and these may explain the challenges of integrating technology into language teaching. Future research should continue to consider how teaching experience relates to technology integration practices and in-class technological pedagogical content knowledge.