The Rapid City Academy is the alternative high school program for South Dakota's Rapid City Area Schools, which has an enrollment of about 13,000 K-12 students, with five middle schools feeding two large traditional high schools and the alternative program. A high percentage of students at the academy are considered "at-risk" due to transient lifestyles, teenage parenthood, high absentee rates, low socioeconomic status, and medical and/or personal challenges that impact their ability to succeed in the traditional classroom setting. Therefore, the academy strives to provide a quality education for its students via alternative instructional methods such as smaller student-teacher ratios, individualized learning plans, strategy-based learning, flexible schedules, and independent and group-led classes. In 2003, Academy teachers and instructional technology specialists developed online courses for implementation in the fall, which led to the debut of the Rapid City Academy Online. This virtual high school is now in its fourth cycle, and has grown to eight teachers, 44 students, and 15 courses. In this article, the authors reflect upon what they have learned about developing and executing a successful online learning environment, and how they have addressed what are frequently seen as the concerns, disadvantages, and limitations of online learning.