Translating university technology via the university–industry route faces an array of challenges. Subsequently, understanding the interrelationships of these challenges hopes to provide a better outlook on the complex nature of the university technology transfer (UTT) process. Such an agenda remains a gap in the domain literature. To advance this oversight, this study intends to identify the UTT challenges and determine their complex contextual relationships. The interpretative structural modeling, together with the MICMAC analysis, was sequentially adopted to derive the overarching structure of the challenges of UTT. A case study in a public university in the Philippines was conducted to carry out these objectives. Findings show that time constraints, knowledge being too theoretical, high costs of managing joint research projects, complex organizational structure, institutional bureaucracy, geographic distance, and lack of national benchmark are driving challenges that influence other challenges in impeding UTT in the representative Philippine university. These findings provide policy insights to key decision-makers and stakeholders on the success of technology transfers.