Contemporary software is increasingly developed using an agile development approach, yet the supplier is generally selected as a result of a waterfall-style competitive tendering and contracting process. The procurement activity may be incompatible with an agile elaboration of requirements and development of functionality, and lead to sub-optimal outcomes. This paper examines the interaction of the procurement and software development lifecycles, explores potential causes of project or system failures and suggests some improvements based on a successful 10 year project between ADI Limited and the Australian Department of Defence.