How Much Does the Hint Matter? Scope Conditions for Hindsight Self-Distillation in Financial Reasoning

Johnny Yu, Cyril Gorlla

Financial institutions operating under data-residency constraints are restricted to open-weight models small enough to locally host, which trail frontier systems on multi-step quantitative reasoning. On-policy distillation narrows such gaps by supervising a student on its own rollouts, but traditional OPD requires a strong external teacher, and on-policy self-distillation (OPSD) conditions on a full reference solution. We ask how much of that signal is necessary. We present Fin-SD, a localized hindsight self-distillation recipe for multi-step reasoning. Given a problem the student fails, the student itself identifies the first incorrect reasoning step and writes a short critique of that step. We truncate the student's trajectory immediately before the error (aiming to obtain a correct prefix), condition a frozen copy of the student on the same prefix plus the hint, and distill that hint-conditioned teacher into the student over a short rollout under reverse KL. No external model contributes a gradient. We apply Fin-SD to GPT-OSS-20B on a custom multi-step financial reasoning benchmark that requires deriving formula inputs from realistic scenarios via accounting conventions. We…