The history of writing is characterised as a ‘tale of adventure which spans some twenty thousand years’, which can offer important insights to help teachers and school leaders better understand writing in classrooms today. The chapter begins by describing the ancient civilisations of Greece and Rome and the vital roots of rhetoric. The Romans’ standardisation of writing is explored, with the great teacher Quintilian exemplifying the best of early writing instruction. The chapter goes on to explore key aspects of Roman rhetoric, including rhetorical devices that exemplify repetition and the careful crafting of sentences. The history of early English schooling – including the first grammar schools – is unpacked, with parallels drawn both with ancient Roman practices and with our modern writing curriculum. Finally, the chapter returns to the modern day, exploring the relationship between current writing habits and technological development. For instance, the shortening and simplification of sentences over time and the less formal writing of pupils may be influenced by technology.