Academic-practice collaborations between academic educators and preceptors are important to ensure the success of clinical education. This study explored the perceptions of academic educators and preceptors on their collaborations in a transition-to-practice program for nursing students. A qualitative exploratory study was undertaken with a purposive sample of 12 preceptors and 13 academic educators across three hospitals and one university in Singapore. Individual interviews were conducted. Four main themes emerged from the thematic data analysis: "hierarchical communication" that prevents academic educators and preceptors from communicating directly with each other, "uncertainty about learning objectives" among preceptors, "discrepancies in clinical assessments" due to a lack of support for preceptors in the assessment process, and "not knowing each other's practice," which could result in theory-practice gaps. The findings reflect the need to strengthen collaborations between academic educators and preceptors through joint teaching and assessments in clinical or simulated settings. This will provide opportunities to learn from each other's practice as well as build rapport, which are critical elements in reducing theory-practice divides and decreasing hierarchical levels between academic educators and preceptors.