The introduction of technology in classroom practices can be challenging if teachers are not encouraged to utilise it in school contexts. Through a self-study methodology, this study investigates a Japanese English teacher’s experiences using technology in classroom teaching. The present study identified both external (first-order) and internal (second-order) barriers to teachers. First-order barriers identified in the Japanese school context involve (a) resources: IT infrastructure and technical support, (b) institution: school policies, classroom sizes and time limitations, (c) subject culture, and (d) assessment: high-stakes examinations. Second-order barriers include (e) teachers’ attitudes and beliefs: a fixed mindset, and (f) knowledge and skills: the lack of professional development. A complicated relationship among teachers was identified as a context-specific issue. This study also discusses further interventions that should be included in the classification of barriers in technology integration at schools.