Managing vulnerabilities in operating systems and software can be challenging and even contentious. Opinions are divided among industry peers – some argue that security updates would be unnecessary if developers were held accountable for security vulnerabilities [1]. In contrast, others assert that updating systems as soon as possible (where applicable) was a critical best practice for users [2]. Most clients in my consulting job adopt some form of vulnerability management paradigm (quarterly vulnerability assessments and addressing discovered vulnerabilities to automated vulnerability management programs where identified vulnerabilities are addressed as soon as possible). I noticed some peculiarities while providing consultancy services to a discerning customer's automated vulnerability management program. The automated vulnerability management product will not be discussed here as it is neither the main focal point nor a debate on whether the product is trustworthy. Instead, it was serendipitous and stemmed from just a simple drive to appropriately mitigate identified vulnerabilities in all systems. Together with the client's management support, we worked together to address the vulnerability in question while ensuring it was fully mitigated.