In teaching, unaddressed countertransference has profound implications for educators and students alike. Consider the story of my past student who experienced heart-wrenching life circumstances during the semester: He lost both parents and became the primary caregiver for his younger siblings. Naturally, his GPA fell significantly under the weight of these responsibilities. With one class left to graduate—a class he had failed six months earlier—he faced an immense hurdle. Together, we brainstormed options. Ultimately, I drafted an email on his behalf to the professor who had previously failed him. This student had been through the worst life could throw at you and was so close to graduating. Wasn’t this the time for mercy? I made my case to my colleague in a quick email and pressed send.