Industry labours under chronic IT skills shortages, despite burgeoning graduate unemployment. This presents a paradox, frequently diagnosed as a simple matter of skills mismatch. Its stubborn persistence, though, notwithstanding decades of sustained interrogation, suggests that a more complex web of factors may be at play. An exploratory literature review of relevant theoretical approaches is undertaken with the aim of expanding the range of factors to be considered in subsequent inquiries into the skills gap. The review proceeds from the specific to the general, interrogating Job Matching Theory, Human Capital and Signalling Theory, Institutional and Resource Dependence Theory, Social and Cultural Capital Theory and Structural Hole Theory. Salient concepts from each are introduced, and their implications extrapolated onto the area of concern. A central theme of trust in the face of uncertainty emerges strongly from the review. Interventions are suggested in the light of these findings.