Evidence of annotations in the home-grown poetry of former Greece dates back to the fifth century (BC), when ‘Iliada’ and ‘Odisea’ were already represented by professional singers/composers, who made entries in the poetry to answer the questions of their audience. As the transition, from a culture of song to a literate society, occurred in this period from the 18th century to the first century and the second century (BC), the annotations were gradually incorporated into the poetic writings. The amount of written annotations on the margins of the medieval manuscripts became huge towards the 10th century. In the first two versions of ‘The Ancient Hero’ at HarvardX MOOC, it was not possible to use the requested annotation tools as a means for a careful assessment of the readings. Using a partial system, we have been able to create apparent annotations in the first reading self-assessment exercises. In the third version, we already have a comprehensive set of text and video annotation tools, developed for HarvardX, including semantic labelling and shared annotations. This system will allow us to have a more effective educational experience, also opening a digital phase in the long history of home-based annotation.