A large body of research has examined the link between personality and face-to-face (FtF) communication knowledge, skills, abilities, and other characteristics (KSAOs). With the rise of digital media, text-based computer-mediated (CM) communication KSAOs have gained increasing attention. We conducted two studies to investigate how personality relates to KSAOs in the different contexts of FtF and CM communication. Contrasting perspectives hypothesize that the results in the FtF and CM contexts would be very similar or distinctly different. In Study 1 (n = 454), an online panel study, the Big Five personality dimensions were assessed and their relationships to FtF and CM communication KSAOs were investigated. Structural equation models and relative weight regression analyses showed that these personality dimensions, mostly extraversion and neuroticism, explained more variance in FtF as compared to CM communication KSAOs. Study 2 (n = 173), conducted in a laboratory context, showed similar results compared to Study 1. In addition, when the Big Five personality dimensions were assessed with a CM frame of reference, more variance was explained in CM than in FtF communication KSAOs. These results point to the importance of considering context effects in communication and in personality research: FtF and CM communication KSAOs need to be differentiated. If not properly contextualized, the relevance of personality and communication competencies in predicting criteria may be underestimated due to contextual mismatches.