Auto insurance rates have been on the rise for several years due to various factors including distracted driving, increased cost of physical damages and serious injuries, and social inflation. To mitigate this impact many companies are implementing telematics programs which helps reduce risk, lower claim costs, enhance fleet operations, and improve driver behaviors. However, implementing a telematics program presents challenges that must be addressed to fully reap its benefits. Identifying these challenges in a construction fleet is crucial for effective risk management and leveraging improved driver behaviors as a valid defense against claims from other parties.