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Anecdotal evidence resulting from an evaluation of a high school cybersecurity curriculum revealed a digital divide between middle and high school learners and Science Technology Engineering Mathematics (STEM) and non-STEM instructors (Gough et al., 2024). Repeatedly, we observed students without Computer Science experience swiftly obtaining proficiency on novel hardware and software used in cybersecurity curriculum while their teachers lagged behind. Similar digital gaps were cited among senior military officers and their junior trainees regarding new media technology (Murphy, 2008). Given that the younger generation of learners is considered technologically inclined due to their early exposure and immersion in technology, we examined the often-cited concept of the digital divide between digital natives and digital immigrants, and its influence on learners’ adaptability to new training technology. Prensky (2001) distinguished digital competence based on the period of birth, that is, either before or after the digital age. However, research indicates that technological competence today is not exclusive to one’s birth period and is influenced by various factors. Aiming to identify these factors, we systematically reviewed 100 scholarly articles related to technological competence, selecting 51 articles for inclusion and data analysis. Results revealed that digital competence is not dichotomous, but encompasses several categories, including digital strangers, digital in-betweeners, digital nomads/cyborgs, and digitally competent users. Further, several factors impact digital competence, including experience with technology, social-cultural dynamics, literacy, geographical location, gender, and socioeconomic status. These findings suggest that the digital divide is of noteworthy discussion for readying a future technologically-driven workforce that may persist long after pre-digital-age instructors retire. Thus, training organizations must understand these factors, evaluate their impact on training processes and learning outcomes, and adapt to ensure effective technology-based training. We present the study’s methods, findings, and practical implications for training and education in technologically driven environments.