It is 5 pm on Friday afternoon. After 2 hours on the telephone trying (and failing) to get her insurance plan to pay for her medication refill, I reached into my pocket and handed the patient $30 so she could fill the prescription. It seemed both kinder and more honest than sending her away saying, “I’m sorry I can’t help you.” While I hardly expected a commendation for such a simple act of kindness, I was completely surprised to find myself being reprimanded for my “unprofessional boundary-crossing behavior” after the resident I was supervising shared this incident with the clinic directors. This allegation of an ethics violation was not only personally painful; it also raised important, controversial, and timely questions about appropriate professional roles.