This chapter reflects on the often uncritical debates about educational policy and the use of digital technologies by schoolteachers that have persisted over the past 30 years. Most commentators have tended to approach digital technology in unrealistic terms--either as having the potential to completely transform schools for the better or herald their imminent demise. This chapter examines these polarised ways of thinking, highlighting a failure to account for the complex, compromised and often 'messy' realities of classroom technology used by schoolteachers. This argument emphasises that critical considerations of the knowledge required by teachers and the context in which they work are necessary to understand the complexity of teachers' technology (non) use. Discussion in the second half of the chapter highlights the need to reconsider 'knowledge' and 'context' as contested terms that are pivotal in examining educational technology policy and practice. Through the introduction of technological, pedagogical and content knowledge (TPACK) framework, the reader is provided with a theoretical lens through which the notions of knowledge and context can be critically explored. [For the complete volume, "Digital Technology, Schools and Teachers' Workplace Learning: Policy, Practice and Identity," see ED573988.]