Considering the speed at which new digital technologies are evolving, this paper aims to investigate the impact of digital transformation on multiple dimensions of literacy. An empirical research using antecedent factors of adoption is conducted to investigate the relationships between factors influencing digital immigrants’ and digital natives’ intentions to use digital technology. Using survey data on 177 digital immigrants and 183 digital natives, structural equation modelling (SEM) and a novel configurational thinking method—fuzzy-set qualitative comparative analysis (fsQCA)—are applied. The results, while showing some similarities, reveal that digital immigrants and digital natives utilize digital technologies differently and their intentions to use are influenced by different factors. For instance, for digital natives, information literacy has no significant effect on intention to use, while this path is significant for digital immigrants. Moreover, fsQCA results, while supporting the SEM findings, show that there are multiple configurations of conditions leading to the outcome of interest—intention to use digital technology.