During clinical practice, students become acquainted with the key work tasks associated with their professions. Students need more support from healthcare educators during clinical practice learning, particularly in challenging situations. This study aimed to describe healthcare educators’ experiences of challenging situations during clinical practice placements. A qualitative study design was used to collect data through interviews with ten healthcare educators from two higher education institutions. The data were analyzed with inductive content analysis. The SRQR reporting guidelines were used to improve the transparency of the study. Educator reactions commonly involved emotional, goal-oriented and pedagogical support towards their students. The interviewed educators felt that mentors – when facing a challenging situation during clinical practice – are tasked with creating an atmosphere that supports student learning. Students faced challenges that were related to self-evaluation, goal-oriented activities, and their attitudes towards feedback. The building of a safe clinical learning environment involves collaboration between students, their clinical mentors and educators.