The successful design, implementation, deployment, and use of mobile software applications is rare. While many mobile apps are developed, few succeed. This design science research project builds and evaluates CrashApp™, a mobile application that connects lawyers and clients before, during, and after car accidents. The effective, widespread use of this app depends on satisfying the needs of three groups of stakeholders – the end-users (clients), the owners (lawyers), and the software developers. The research objective is to investigate the key differences among the three stakeholder groups on evaluation criteria for mobile app success. Evaluation strategies and methods are selected to collect data that measures each group’s satisfaction with the constructed application artefact. Research contributions are the identification of multiple stakeholder groups and the ability to design rich evaluation strategies that provide measures of application success. Practice contributions are the design and development of a useful mobile app that provides needed services to the client and effective client connections for the law firm to interact with the clients. The project produced an instantiation of the design artefact CrashApp™ mobile application, which was evaluated with a naturalistic evaluation approach, including the following methods and techniques: focus groups, focused surveys, usability surveys, and real life tests and assessments.