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Law schools make “pro bono” opportunities available to students to introduce them to the responsibilities of the profession. Often these pro bono law students help in “brief advice” projects staffed by volunteer attorneys. This staffing-supervision structure presents challenges in ensuring clients receive competent, individualized advice and the students receive adequate oversight so that this is a positive learning experience for them. This paper analyzes transcripts from 46 recorded student-client interviews and 35 student-attorney consultations. It focuses on those cases where there were “errors or omissions” -- either the client got some erroneous advice or the client did not receive complete, personalized advice -- and asks why. Conversation Analysis allows a fine-grained analysis of the interview, the student-supervisor consultation, and the final client counseling. This analysis shows where the break-downs occurred and theorizes why. The paper ultimately proposes techniques to improve the operation of a brief advice site staffed by students.