This exploratory article analyses an extra-curricular pedagogical digital media exercise conducted at the Department of Communication and Art of the University of Aveiro, in Portugal. This exercise’s goal was to encourage students to critically analyse and interpret Helena Cardoso's body of work and recreate it through contemporary digital media. This initiative is part of an ongoing PhD research project which aims at inscribing the work of the designer Helena Cardoso in the History of Portuguese Design. The exercise began with a brief presentation of the work done by Helena Cardoso after the revolution of 25th April 1974. This allowed students to expand their knowledge of previous generations of Portuguese designers and develop their visual culture. The students in this educational context produced results that converged in a visual and conceptual analysis. Through participant observation, the researcher conducted the exercise and registered the semantic field employed by the students during the visual analysis. This workshop provided the students with the opportunity to apply knowledge already acquired in various curricular units. The results demonstrated a plurality of approaches, in both visual and conceptual aspects, as well as in the technological resources employed. It brought a new impetus to Helena Cardoso's work, providing new narratives created by a generation of digital natives.