Various driving forces originating from society, government, employees, and partners are forcing the enterprise to both incorporate sustainable development in its internal operations and practices, and to align these with the principles thereof. Technology-oriented project management, as a core competency of many enterprises, is not excluded from these requirements. Four cases are explored of how the aspects of sustainability have been addressed by various approaches and tools to enhance the performances of enterprises—in the context of project management in South Africa. The associated challenges are highlighted and the requirement for further work, to address the shortfalls, is outlined. Specifically, by developing methods for understanding the full implications of alternative choices and their relative attractiveness in terms of enhancing the resilience of systems, by extending the field of sustainability science into the field of project management.