Building on experience teaching the transcription of early modern Japanese texts in a Japanese university, this show and tell presentation will explore different ways to implement the use of digital tools in the classical (early modern) Japanese classroom. The presentation will cover tools for study, tools to help decipher texts, and the growing body of AI-powered transcription tools such as Miwo and Minna de Honkoku focusing particularly (though not exclusively) on educating students in how to transcribe and decipher early modern Japanese texts. Critically reflecting on the use of these tools and their limitations, the speaker will seek to illustrate that the use of digital tools is highly beneficial in the classical Japanese classroom.