This research examined digitalisation as a transformative elixir to the school-not-to-job conundrum in Nigeria, with analytical focus on four critical variables: digital skills acquisition, digital entrepreneurship, ICT-based learning, and internet accessibility. Graduate unemployment remains one of Nigeria’s most debilitating socioeconomic crises, as the structural disconnect between educational attainment and labour market absorption, continues to deepen despite annual increases in tertiary institution output. Drawing on an extensive review of extant literature, empirical studies, and policy documents spanning 2015 to 2025, the study adopts a conceptual-analytical methodology situated within the Human Capital Theory as its primary theoretical framework, with the Technology Acceptance Model providing complementary explanatory power. The paper finds that digital skills acquisition significantly enhances graduate employability across all disciplines and institutional types; that ICT-based learning environments improve employment readiness when adequately implemented; that digital entrepreneurship offers a viable, scalable pathway to self-employment and income generation; and that internet accessibility functions as the foundational enabling condition for all other dimensions of digitalisation. The study further argues that every Nigerian undergraduate must acquire at least one or two marketable digital skills before graduation, thereby reducing dependence on increasingly scarce white-collar employment. Significant barriers including infrastructural deficits, curricular rigidity, digital divides, and cultural orientations towards formal employment are identified and interrogated alongside considerable prospects for progress. Five actionable recommendations are advanced for government, educational institutions, the private sector, and individual graduates to collectively harness digitalisation as a credible and sustainable solution to Nigeria’s school-not-to-job crisis.