The rapid expansion of digital technologies has created new opportunities for young people to generate income. Many youths now rely on digital platforms, freelance tools, and online services as alternative means of earning a living. However, growing evidence suggests that exposure to digital income tools may also create pathways into cybercrime. This study investigates how legitimate digital hustle gradually transitions into cyber-related crimes among youths in Lagos State, Nigeria. A quantitative research design was adopted, and data were collected from 275 respondents selected from three local government areas in Lagos State using a multistage sampling technique. Structured questionnaires were used to collect data, and the results were analyzed using descriptive statistics and regression analysis. The study reveals three major findings. First, exposure to digital income tools significantly increases youths’ technical confidence and knowledge of digital systems. Second, persistent income pressure encourages the shift from legitimate digital activities to illegitimate cyber practices such as account hacking and online fraud. Third, peer learning networks within digital communities accelerate the transition from online hustle to cybercrime participation. The study concludes that cybercrime among youths is not simply a criminal choice but often an unintended outcome of economic survival strategies in digitally mediated environments. The study recommends youth-focused digital entrepreneurship programs, ethical technology training, and stronger cyber awareness initiatives to redirect youth digital skills toward legitimate economic opportunities.