Digital tools are increasingly used in cultural astronomy, so that it is now more important than ever to assess their precision and reliability, and to identify what uncertainties they may introduce. The present work aims to address these issues by comparing a dataset of orientations of Roman cities in the Iberian Peninsula measured in situ with measurements of the same structures obtained through different digital tools. By this, it is possible to estimate the errors that using these techniques introduce and to establish precision limits to data in future work. The results of this preliminary study are then implemented in an archaeoastronomical research project in North Africa, where some on-site measurements had been made in previous fieldwork campaigns by members of the group prior to the current political unrest that now prevents work at some sites in the region. In these instances, Google Earth Pro (2017) and HeyWhatsThat (Kosowsky 2012) have been key tools that have allowed us to complete a survey stretching from present-day Morocco to Libya, as well as to extract a preliminary outline of orientation trends in Roman Africa.