The intelligible world of machines and predictive modelling is an omnipresent and almost inescapable phenomenon. It is an evolution where human intelligence is being supported, supplemented or superseded by artificial intelligence (AI). Decisions once made by humans are now made by machines, learning at a faster and more accurate rate through algorithmic calculations. Jurisprudent academia has undertaken to argue the proposition of AI and its role as a decision-making mechanism in Australian criminal jurisdictions. This paper explores this proposition through predictive modelling of 101 bail decisions made in three criminal courts in the State of New South Wales (NSW), Australia. Indicatively, the models’ statistical performance and accuracy, based on nine predictor variables, proved effective. The more accurate logistic regression model achieved 78% accuracy and a performance value of 0.845 (area under the curve; AUC), while the classifier model achieved 72.5% accuracy and a performance value of 0.702 (AUC). These results provide the groundwork for AI-generated bail decisions being piloted in the NSW jurisdiction and possibly others within Australia.