Many road authorities recognize the challenges associated with a reactive approach in road safety and have adopted a proactive and systematic approach in their road safety initiatives. However, automation is a key challenge road authorities face in implementing an efficient and effective traffic safety management program. In the summer of 2009, American Associated of State Highway and Transportation Officials released the first version of SafetyAnalyst software, and in 2010 published the Highway Safety Manual. The Highway Safety Manual provides road safety knowledge and tools in a practical form to facilitate improved decision making based on safety performance. The focus of the Highway Safety Manual is to provide quantitative information for decision making. SafetyAnalyst software incorporates methodologies set forth in the Highway Safety Manual for road safety management in computerized analytical tools. These tools support the identification of safety improvement needs and the decision making process for developing a system-wide program of safety improvement projects. The Ministry of Transportation of Ontario has initiated a project to configure SafetyAnalyst to meet their needs’ in managing the road safety analysis of their highway network. In this initiative, all six SafetyAnalyst modules including the Network Screening Tool, Diagnosis Tool, Countermeasure Selection Tool, Economic Appraisal Tool, Priority Ranking Tool, and Countermeasure Evaluation Tool are configured for the Province of Ontario road network. As part of this initiative, the Ministry’s Safety Performance Functions are being updated for road sections, interchanges, ramps, ramp terminals, and intersections. The functional forms of these safety performance functions are compatible with those of SafetyAnalyst. Moreover, the SafetyAnalyst modules are configured with Ontario’s customized values. The main goal of this paper is to summarize the lessons learned in this initiative to assist other road authorities in their prospective undertakings related to SafetyAnalyst. This paper highlights challenges associated with compiling infrastructure data, traffic volume data, collision data, importing data into SafetyAnalyst while keeping the road authority’s databases unchanged, Safety Performance Functions in SafetyAnalyst, and customized values for various modules in SafetyAnalyst. This paper provides solutions to address these challenges. It also recommends the necessary steps for road authorities before starting an initiative to configure SafetyAnalyst for their network.