The purpose of this study was to investigate the impact of student success technology (SST) on student engagement at a university from the perspectives of students and academic advisors. Specifically, this study examined the relationship between external variables such as educational initiatives and unforeseen events and student engagement and the influence of the digital divide, perceived usefulness (PU), perceived ease of use (PEOU), and acceptance of this relationship. The overall conceptual framework for this study was guided by the modification of the technology acceptance model (TAM). Based on the extended TAM, the impact of WSUP Connection student success technology and the COVID 19 pandemic (unforeseen event) on student engagement (measured by the number of appointments made by students and the number of communication messages sent by academic advisors) was examined. Data on the number of appointments and communications involving 9,703 students and 58 academic advisors from the 2017-2018 academic year through the 2020-2021 academic year were drawn from the WSUP Connection platform. Data on the digital divide, PU, PEOU, and acceptance were drawn from the WSUP Connection surveys involving 151 students and 17 academic advisors conducted in December 2021. [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.]