The specificity of project management in different contexts and industries is recognized, but little empirical research encompasses a sufficiently broad range of contexts and project types to precisely identify these specificities. This article adopts such a wide perspective based on a large sample of data from an ongoing empirical investigation of project management practice. Contextual archetypes are identified (i.e., clusters of experienced practitioners that share similar organizational and project contexts). Archetypes of contextualized practice are then investigated through the study of the extent of use of empirically identified toolsets in each cluster. The results empirically confirm some well-known assumptions about practice but also sharpen the knowledge and understanding of practice in real complex multidimensional contexts. A new concept of “performing-maturity” emerged from the data. This concept sheds light on the entangled imbrications of maturity, competence, and success. Practices are regressed against performing-maturity to reveal best contextualized practices.