The benefits of project, program, and portfolio management software toolsets can be enhanced through training. Little is known about the realization of positive, beneficial outcomes and Project Management Information System (PMIS) training. This research seeks to improve understanding of project management software toolset training practices and outcomes. This study examines the prevalence, effectiveness, and impact-per-hour efficiency of training in real-world organizations. We further explore relationships between individual and organizational characteristics and training outcomes. Formulae for estimating training costs are derived using regression modeling. Surveys were collected from 1,021 active professionals and analyzed using quantitative methods. Research participants were practitioners recruited by eight different companies, industry groups, and professional organizations within the PMIS community. The findings of this research indicate significant differences in utilization, efficacy, and efficiency of PMIS training in practice. The outcomes and methodologies of this study are being incorporated into ongoing research that focuses on improving PMIS training delivery, evaluation, and planning. The outcomes of this research may result in more effective, efficient, and economical PMIS training that is better tailored to the unique needs of each organization.