In this qualitative single-case study, this researcher explored the challenges faced by online advisors and their need to have a training program that is beneficial to online academic advisors. The purpose of this study was to explore the perceptions and experiences online advisors had regarding challenges they faced and the on-the-job training they received for their positions. Three approaches to data gathering were used for this case study: (a) a distinct situation, (b) triangulation, and (c) the prior development of theoretical propositions that guided data collection and analysis. The challenges online advisors faced and the training they received were explored through the perspective of 14 online advisors who were members of the National Academic Advising Association. The targeted goal for the study was 20 participants; however, data saturation was met after 14 participants completed the questionnaire, which contained 20 multiple choice and true/false questions. The online questionnaire was uploaded to Survey Monkey's website. Qualified participants were emailed a link to the questionnaire once their pre-screening was completed. NVivo software was used to analyze data. Findings from this study aligned with previous research regarding the challenges online advisors faced and the specialized on-the-job training online advisors received for their positions. However, some differences were noted. The results of the study indicated that because of the growing number of people entering colleges and universities and the connection found in the advisor-advisee relationship, it is necessary to understand the challenges online advisors face and the type of training and resources that are needed to make online advisors effective in their positions. The researcher's aim was to gain further understanding of the needs of online advisors in order to assist administrators in their development of online training programs. Future research is needed in order to fully understand the online advisors' needs and to create an effective training program. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]