In this paper we provide an account of how we ported a text and data mining course online in summer 2020 as a result of the COVID-19 pandemic and how we improved it in a second pilot run. We describe the course, how we adapted it over the two pilot runs and what teaching techniques we used to improve students’ learning and community building online. We also provide information on the relentless feedback collected during the course which helped us to adapt our teaching from one session to the next and one pilot to the next. We discuss the lessons learned and promote the use of innovative teaching techniques applied to the digital such as digital badges and pair programming in break-out rooms for teaching Natural Language Processing courses to beginners and students with different backgrounds.