In recent years, life drawings as a tool for site survey had slip into the oblivion of time. Its use is considered anachronistic and superfluous in what is defined as the ‘digital age’. Nevertheless, thanks to architecture students, who measure themselves with this type of competence, freehand drawing survives revealing its role in understanding the existing reality. Furthermore, the pandemic emergency has provided the opportunity to reflect on the subject, highlighting the importance of urban sketching as a tool to understand and comprehend the building environment. However, the need to adapt to remote activities has inevitably led to the development of new and interesting methodologies by renewing the practice of sketching and providing, at the same time, a series of reflections on the possible relationships between drawings made with the pencil and the processes of digitization. Therefore, this paper dwells on recent experiences, teaching methods, and transfer of research activities results, focused on the architectural heritage observation through sketching. In particular, the exercises carried out during the quarantine period, through distance learning, became an opportunity to reflect on the scenarios of cyclic contamination – rather than dichotomy – of the analogic-digital binomial.
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