Holiness missions is an area of mission history that is often understudied, yet it can provide insight into the growth of the Church in various parts of the world. This article examines the life of Sidney W. Edwards, a Holiness missionary who was a key part of H. C. Morrison’s missionary efforts. He served as the missionary of a mission H. C. Morrison founded in Cuba, as one of the first Holiness missions in the Caribbean. He then went on to serve in Puerto Rico with the Methodist Episcopal Church in planting churches in some of the mountainous regions of that island. Finally, Edwards became the pioneer missionary for the Methodist Episcopal Church in Costa Rica, almost single-handedly starting the Methodist Church in that nation and running it until various problems and a scandal led to his leaving the mission field, Edwards was also involved in a very early evangelistic tour of Central America, and so he becomes a key figure in the early mission history of the Spanish-speaking Caribbean and Central America. His story helps illustrate the problems Holiness missionaries faced in terms of finances, leadership of the mission, and dealing with family issues from the mission field. His example also demonstrates how early Holiness missionaries sometimes made the decision to become part of more traditional denominational mission agencies.