Small to Medium Enterprises (SMEs) represent a large proportion of any country’s business activity, and their contribution to national supply is significant. There are many studies and reports revealing the threat to business from cyber security issues resulting in system penetration and information compromise. Very few studies are focused on evaluating SME cyber security postures. Even fewer are focused on directly surveying the actual SMEs themselves about the issues they face. Utilizing these type of survey results to improve SME outcomes with respect to cyber security is even rarer still. This chapter outlines an approach currently being undertaken in Western Australia with SMEs in the northwest metropolitan region of Perth, specifically within the large local government catchments of Joondalup and Wanneroo. The high-order goal of the project is to assist with measures to improve their cyber security resilience and resistance to threats for SMEs in these catchments.