This case engages students by featuring a relatable scenario of a new accounting professional being asked by a friend for help filing his individual tax return. The friend's return is more complex than expected because of unclear filing requirements related to his discharged student loan debt and his disability status. An amended return may be needed for a previous year, in part because of a reportedly erroneous W-2 from a former employer; and taxpayer withdrawals from an employer-sponsored tax-deferred savings account. Requirements include researching and documenting federal tax law, using judgement to make recommendations within the context of conflicting information, and evaluating the ethical implications of a friend's assistance as well as professional codes of conduct. Students are also asked to write a client memo. This case will be of particular interest to students who are considering tax careers. It is appropriate for undergraduate and graduate tax courses.