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Learning management systems (LMSs) are the technical foundation for online learning programs that offer benefits to learners in a variety of settings. As with many enterprise software systems, LMSs are expensive and carry considerable risk. Exploring critical success factors (CSFs) and using them as a foundation for decisions concerning complex software implementations helps increase the likelihood of success. This study addresses the gap in knowledge concerning CSFs for LMS implementations. The purpose of this phenomenological study was to discover CSFs by exploring the lived experiences of 8 association executives who identified themselves through email communications as having managed a successful LMS implementation. Organizations providing online continuing education programs were identified using a publicly available list, and program managers were identified from the organization's website. Interviews using semi-structured questions yielded a set of tightly correlated CSFs from 6 of the 8 participants. General systems theory and sociotechnical systems theory underpinned the study. Moustakas' data analysis methods were used to code the interviews and develop themes, which resulted in a set of actionable CSFs. Stakeholder support, a well-planned implementation, an experienced vendor, and software that provides a predictable user interface were among emergent CSFs for LMS implementations. This research may have a positive social impact because reducing the risk of LMS implementations will enable organizational leaders to extend learning opportunities to more individuals. Those opportunities, in turn, will lead to prosperity for membership associations and the industries they serve.