Unlike the studies of freshmen entrants, the learning experiences of community college transfer (CCT) students in the receiving university is a topic that has only started to gain attention in recent decades. Little is known about the differences between CCT and freshmen entrants with regard to their study workload stress and its relationship with their perceptions of the teaching and learning environment, approaches to learning, self-efficacy and generic skills. The purpose of our study was to address this gap. This was a cross-sectional survey study conducted from April 2018 to November 2018 in a university in Hong Kong. The HowULearn questionnaire was adapted to local usage and validated for data collection. In total, 841 CCT students and 978 freshmen entrants completed the survey. The respondents were aged between 19 and 52 years (mean = 21.6, SD = 1.92), and 66.0% were women. The HowULearn questionnaire was determined by factor analyses to have eight factors. The reliabilities of the eight factors were found to be acceptable (Cronbach alphas = 0.709-0.918). The CCT students scored significantly higher than the freshmen entrants for perceived study workload stress and surface approaches to learning, but lower on teaching for understanding & encouraging learning, peer support, and self-efficacy beliefs. The surface approach to learning, deep & organized studying, alignment & constructive feedback, and generic skills were found to be predictors of study workload stress in both groups of students, and in the overall student data. This study has shown that CCT students and freshmen entrants differed with regard to their study workload stress and learning experiences. Our findings provide a message, both for educators in higher education and policy makers in the government-there is not a one-size-fits-all approach to different student populations when it comes to enhancing their learning experiences.