Globally, the degree to which educational practices have been digitalized varies significantly. Many countries in sub-Saharan Africa, including Seychelles, are beginning to integrate digital tools into their educational systems and developing ICT (Information and Communication Technology) policies. Sweden, on the other hand, has experienced extensive digitalization of education for many years, and is already in a state of politically driven de-digitalization. This article argues that there are conclusions to be drawn from the massive digitalization and subsequent de-digitalization of education in Sweden that may be relevant for digitalization policies in sub-Saharan African contexts where such policies can still be adjusted in order to avoid sharp dichotomies between digital and analogue tools. Drawing on two studies in Swedish classrooms – Grades Four and Eight – this paper examines how digital pencils can function as boundary objects that mitigate digital-analogue dichotomies. The analysis shows how digital pencils can function as boundary objects that connect digital classrooms – as are most Swedish classrooms – to (previous) analogue literacy practices, such as writing and drawing by hand. Importantly, the paper also argues that digital pencils can probably function as boundary objects that facilitate the transition of analogue literacies into more digital ones in African contexts, without disconnecting from the use of pencils and paper.