Global Software Engineering (GSE) research contains few examples consciously applying what Glass and colleagues have termed an ‘evaluative-critical’ approach. In this study we apply dilemma analysis to conduct a critical review of a major (and ongoing) nearshore Business Process Outsourcing project in New Zealand. The project has become so troubled that a Government Minister has recently been assigned responsibility for troubleshooting it. The ‘Novopay’ project concerns the implementation of a nationwide payroll system responsible for the payment of some 110,000 teachers and education sector staff. An Australian company won the contract for customizing and implementing the Novopay system, taking over from an existing New Zealand service provider. We demonstrate how a modified form of dilemma analysis can be a powerful technique for highlighting risks and stakeholder impacts from empirical data, and that adopting an evaluative-critical approach to such projects can usefully highlight tensions and barriers to satisfactory project outcomes.