Rainwater harvesting is a simple and effective tool to collect and store water for domestic and institutional use. In developing countries, captured rainwater can be used to replace or supplement government-supplied or manually-transported water. A rainwater harvesting system consists of a catchment area, gutter, and storage tank. Gutters typically have a V-shaped, trapezoidal or rectangular cross-section. This work presents a case study on the design and performance analysis of three conventional and one novel, “wrapped” gutter cross-section along with the implementation of a novel gutter design in the developing world. A Team of undergraduate students performed the design and analysis and, though a service-learning experience in May 2013, investigated barriers to implementing rainwater harvesting in central Kenya. It was found that while gutters can be easily fabrication and installed using locally-available materials and skill-sets, for consumer, the potential return on investment was low and the cost of implementation was high. For producers and installers, non-uniform roof designs and conditions was a major obstacle.