Strategies that have worked to offset high attrition rates and retain students in traditional institutions of higher education are not necessarily applicable within an online learning environment. As a result, not only is student attrition more likely to occur in the online environment, but traditional classroom retention strategies are less likely to be effective. The shortcomings in predicting student success in online learning suggests that the methods used to assess student performance have been inadequate. Research in both traditional and online education has shown that students with specific personality types may be more likely to excel within the classroom. Therefore, this study explored students' personality types in relation to online course success in order to isolate personality types that may be more likely to succeed in an online learning environment. A comparative case study was used to compare a sample of community college business students who have been successful in online learning environments and those who have not been successful. This study uses the classical DISC survey instrument in conjunction with one-on-one interviews. The findings indicate that personality type cannot be used to predict online course success. Results suggest that student characteristic behaviors, rather than simply personality type, although likely related, may be more relevant to community-college student success in an online learning environment. In addition, findings from the study reveal the potential benefits that student technology can provide, including support for students new to online learning and increased levels of collaborative learning and communication. These particular elements could be implemented as part of the required curriculum for online courses. It is recommended that educational leadership potentially use these results to support improvement in student success in an online environment.