There exists an abundance of marketing literature centred on how everyday brands can successfully execute brand extensions into new or similar categories to their parent brand. The majority of this research body focuses directly on the parent brand's influence on the extension, such as how an extension benefits from being associated with a renowned brand, the emotional attachment from loyal consumers, and the immediate equity generated by consumer familiarity with the parent brand's experience overall. A starting assumption of such work is the success of the parent brand. While this type of brand extension has received important attention, there is considerably less understanding of brand extensions from brands that are negatively evaluated, that launch extensions outside of their core category. In such cases, the brand extension may contradict or rival that of the parent's core business. In effect, this is exactly the case when brands operating in stigmatized industries such as gambling, alcohol, or cigarettes attempt extensions into comparatively-more upstanding categories. Examples of such circumstances include that of oil companies pursuing greener or more sustainable products, or cigarette manufacturers offering reduced-harm or smoking cessation solutions under different brand extensions. In response to environmental sustainability efforts, pro-health movements, and other social issues, stigmatized brands operating in the gambling, oil, or tobacco industries must evolve to stay relevant with increasingly critical consumers. Their actions are likely to be met with consumer scepticism, with the potential of the core stigma of their past and current operations transferring to comparatively virtuous commercial attempts, including that of a brand extension. Scant marketing literature exists to understand how consumers may evaluate virtuous or upstanding extensions by stigmatized brands. That is, an extension intended to rival or oppose the stigmatized category in which its parent-brand operates, and where its notoriety and stigma has principally been formed. This research explores the complexities of comparatively virtuous brand extensions (CVBEs) by stigmatized parent-brands and examining how extant research on successful brand extensions applies in this scenario. Specifically, I examine the dynamics of commonly-accepted brand extension success drivers in the context of a stigmatized brand attempting comparatively virtuous extension. The drivers themselves range from material measures such as marketing support and retailer acceptance, to more perceptual measures that connect the parent brand to the extension such as degree of 'fit', authenticity perceptions, and parent brand conviction and experience. Extant literature suggests that successful brand extensions are heavily influenced by a downward influence of the successful and positively perceived parent brand on the extension. In the case of this study, given the stigma associated with the parent brand, one must assume that no positive association would be transferred, jeopardizing the success and consumer perception of any extension attempt. This relationship also builds on the concept of brand stigma and the role it plays on extensions by stigmatized brands. By way of qualitative methods leveraging archival data, the findings show that the drivers of brand extension success based on the renown of the parent brand differ in the way they are represented for stigmatized brands and CVBEs. Most importantly, the relationship differs in the direction of the influence, where a CVBE viability depends on the influence it has on the parent brand. That is, how the extension's positioning and overall marketing message is leveraged by the parent brand. This introduces a new relationship to our current understanding of brand extensions: an extension's upward effect on the parent, with the study's findings indicating such a brand extension can work as a vehicle to de-stigmatize the parent brand. This concept contrasts the extant literature which has mainly posited the downward influence of the parent brand on the extension.