This article adopts a psychological lens to investigate whether cognitive biases might obscure insolvency practitioners’ perceptions. Through an experimental study among members of INSOL International (N = 272), we find that insolvency practitioners’ judgments of business valuations and business valuators in an insolvency situation are affected by (1) the degree of perceived similarity with the valuator (i.e. similarity bias) and (2) the outcome of a bankruptcy deal in which a valuation is used (i.e. outcome bias), such that their judgments are more favourable in case of higher perceived similarity and in case of a positive outcome. Furthermore, we find that male insolvency practitioners have more trust in male valuators than in female valuators, suggesting that (3) gender biases play a role as well. These findings shine a light on decision-making in business rescue and bankruptcy cases and the insolvency industry in general. The findings call for further research on cognitive biases in insolvency-related matters including possible implications for policymakers.