The purpose of this study was to examine which engagement factors, along with students' socio-demographic characteristics and educational background, were associated with students' overall satisfaction with their current 4-year institution. It also aimed to identify whether these independent variables had similar or different associations with the likelihood of being satisfied between vertical and horizontal transfer students. This research study first employed descriptive statistics to provide a thorough overview of the samples of the study, and then performed exploratory factor analysis (EFA) to identify engagement factors. Lastly, this study tested logistic regression models to identify factors associated with students' satisfaction for vertical and horizontal transfers, respectively. The study findings highlight that coursework emphasizing on a higher order of thinking, student-faculty interactions, and institutional support were important engagement measures contributing to the likelihood of being satisfied for both transfer groups, but having serious conversations with students of different backgrounds was negatively associated with vertical transfer students' satisfaction only. This study provides meaningful insights into transfer students' college engagement and satisfaction, and addresses the gap in the existing literature on diversity and complexity among transfer students.