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Post-bankruptcy entrepreneurs (PBEs) often face a social stigma that limits their access to financial resources from banking partners and their ability to embark on new business ventures. However, some PBEs do manage to obtain financing from banks when they start a new business. In this article, we seek to understand the conditions under which loan officers sometimes place their trust in a PBE, despite a negative first impression of the entrepreneur’s funding application prompted by their previous failure. To do this, we draw on Mayer et al.’s (1995) model of the antecedents of interpersonal trust. We also employ a qualitative approach, based on semi-structured interviews with twenty-seven bankers (stigmatizing actors) and entrepreneurs (stigmatized actors). The analysis of our empirical data, using the methodology put forward by Gioia et al. (2013) first allows us to better understand the stigmatization of PBEs (origin, manifestation, reinforcing or mitigating elements), as well as the mistrust they are spontaneously subjected to by loan managers at the time of entering into the business relationship. Our results then show that a process of de-stigmatization of PBEs can nevertheless emerge during the discovery interview. As such, we highlight, in the form of a four-step decision tree, the banking engagement technology that allows loan officers to overcome their initial prejudices and be reassured about the perceived integrity and capacity of an entrepreneur, despite past business failures.