Globally, there is an increasing prevalence of higher education students with mental health issues. Educators are guaranteed contact points, and students often seek their support to manage their mental wellness. However, there is limited research describing educators' experiences of these interactions. This interpretive phenomenological study engaged 16 educators from an institution in Canada and Australia. Interviews were conducted to understand their lived experiences interacting with and supporting students with mental health issues. Data demonstrated that educators encountered students with challenges to mental wellness, most commonly around course assessments. These encounters caused strain on educators personally and professionally, which they responded to by adapting teaching practices to mitigate risks to student and educator wellbeing, compartmentalization and boundaries, and relational connection and support. Over time they evolved to manage this and incorporate this role into their teaching, with more confidence and less impact on themselves. This manuscript highlights the lived experiences of educators engaging with students with mental health stressors, and provides tangible examples of professional and personal modifications that mitigated the strain on the educator caused by these encounters.