This paper reports on the development of a prototype solution for tracking and monitoring shipping containers. Deploying wireless sensor networks (WSNs) in an operational environment remains a challenging task. We strongly believe that standardized methodologies and tools could enhance future WSN deployments and enable rapid prototype development. Therefore, we choose to use a step-by-step approach where each step gives us more insight in the problem at hand while shielding some of the complexity of the final solution. We observed that environment emulation is of the utmost importance, especially for harsh wireless conditions inside a container stacking. This lead us to extend our test lab with wireless link emulation capabilities. It is also essential to assess feasibility of concepts and design choices after every stage during prototype development. This enabled us to create innovative WSN solutions, including a multi-MAC framework and a robust gateway selection algorithm.