Higher education institutions (HEIs) have experienced severe cutbacks in funding over the past few years, with universities examining options for alternative funding streams, such as alumni funding. Identifying the factors influencing their alumni's intentions to invest in their alma mater can be of significant importance when establishing a sustainable revenue stream. Within this context, empirical research on the potential role of trust is scarce. This paper aims to deepen the analysis of the relationship between alumni trust and engagement as well as three outcomes, namely support, commitment, and attitude toward donation. A structural equation model was tested on two samples of US (n = 318) and Italian (n = 314) alumni. Although both countries are affluent and developed countries, the USA has an established tradition of alumni donations, which is not such a developed practice in Italy. For both countries, results confirm that engagement is an antecedent of trust, which in turn leads to the three investigated outcomes (support, commitment, and attitude toward donations). In contrast, the effect of commitment on attitude toward donations is significant only for the USA universities. The paper has interesting theoretical and managerial implications. From a theoretical point of view, the study aims to address a gap concerning the role of trust in the HE context. Managerially, the study has significant implications for universities that want to change alumni attitude toward donations.