Regulators consider lack of professional skepticism to be a major cause of audit deficiencies and are concerned that auditors are more willing to accommodate less conservative accounting policies in clients employing a former partner of their firm because of diminished skepticism. This study examines the impact of audit firm alumni serving as senior members of client's management on auditors' skeptical judgment. In a controlled experiment with three different conditions, audit managers assessed the potential impairment of goodwill. The results indicate that auditors are more likely to make a judgment that agrees with the client's position when the CFO is a former engagement partner from their firm, and are more confident in the CFO's position when the CFO is a former Big 4 partner, whether from their own firm or another firm, than when the CFO is not identified as having any affiliation with any audit firm. Together, these results suggest that there is an alumni effect and that the effect is also partially influenced by the differing levels of auditor's confidence in the CFO's position, as a consequence of the CFO's known or unknown affiliation with Big 4 firms.