This study examines the effectiveness of implementing a chatbot solution to supplement existing student support or service models on campus, specifically for transfer students. Chatbots, an artificial intelligence solution meant to mimic human conversation and personality, have been viewed as a viable option for supporting transfer students throughout their journey in higher education. With the influx of first-generation students, non-traditional students, and transfer students, institutions want to ensure that they have tailored solutions to meet the needs of all populations. Chatbots may be a potential solution. This study begins more broadly with contextual evidence that demonstrates that low student satisfaction among other factors can lead to not enrolling in or graduating from a college or university, highlighting more specifically transfer students as a vulnerable population. To address this problem, this study explores the potential of innovative, web-based solutions, such as a chatbot, for assisting institutions in providing timely answers to transfer students navigating the college process. The hypothesis is that the chatbot solution will lead to higher student satisfaction for transfer students. To determine the merit of this hypothesis, the study evaluates the use of a chatbot on the website of a large, public community college that has a strong focus on transferring students to four-year, bachelor-degree granting institutions. This evaluation uses the college's chatbot preliminary launch utilization data and student survey responses to determine the overall impact on student satisfaction. Based on the observations and results of this evaluation, this study will conclude with findings and recommendations for future work with chatbots as a tool for transfer student success. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]