Cybercrime in West Africa has transcended petty online scams to emerge as a complex, organized threat with profound implications for regional security and governance. Nowhere is this more evident than in Nigeria, where the rise of internet fraud popularly associated with the “Yahoo boys” has evolved into a deeply embedded socio-economic and cultural phenomenon. This paper explored the conditions under which digital crime flourished, tracing its connections to structural unemployment, state fragility, global neoliberalism, and the aspirational subcultures of marginalized youth. By interrogating the gaps between legislation, enforcement, and social legitimacy, the analysis revealed the limitations of Nigeria’s Cybercrime Act of 2015 in combating fast-evolving digital threats. Ethnographic perspectives and interdisciplinary sources enriched the discussion, highlighting how cybercriminals appropriated symbols of resistance and modernity to justify their actions. The implications extended beyond domestic concerns, as cybercrime networks increasingly intersected with global financial fraud, identity theft, and transnational insecurity. Evidence pointed to a convergence of digital technology and state failure, raising critical questions about sovereignty, policing, and trust in public institutions. In response, the study called for coordinated regional cybersecurity frameworks, investment in youth-centered digital literacy, and more holistic strategies that treat cybercrime not just as a legal anomaly but as a symptom of deeper socio-political fractures. The findings contributed to criminological debates on deviance, informal economies, and digital governance in postcolonial African contexts.