It is becoming more common these days (though still not common enough) for organizations to have regular vulnerability scans conducted against Internet-facing, and sometimes internal, systems and devices. This is certainly a step in the right direction, as monthly scans against the network and service layer are an important control that can be used to detect missing patches or weak configurations, thereby prompting vulnerability remediation. Perhaps unsurprisingly, some application security vendors are applying this same principle to web application testing, insisting that scanning a single application numerous times throughout the year is the best way to ensure the security of the application and related components. Does this approach make sense? In a handful of cases, where ongoing development is taking place and the production version of the application codebase is updated on a frequent basis, it may make sense to scan the application prior to releasing changes (i.e. as part of a pre-deployment security check). Additionally, if an organization is constantly deploying simple websites, such as marketing “brochureware” sites, a simple scan for vulnerabilities may hit the sweet spot in the budget without negatively impacting the enterprise’s risk profile. However, in most cases, repeated scanning of complex applications is a waste of time and money that offers little value beyond identifying the more basic of application weaknesses. Large modern web applications are intricate pieces of software. Such applications are typically updated based on a defined release cycle rather than on a continual basis and, when they are updated, functionality changes can be substantial. Even in the cases where updates are relatively small, the impact of these changes to the application’s security posture can still be significant. Due to these facts, repeated scans for low-level vulnerabilities simply do not make sense. Rather, comprehensive testing to identify application-specific weaknesses, such as errors related to business logic, is necessary to truly protect against the real threats in the modern world. Your doctor might tell you to check your blood pressure every few weeks but he would never lead you to believe that doing so is a sufficient way to monitor your health. Rather, less frequent but still regular comprehensive checkups are recommended. So why would you trust an application security vendor that tells you that quantity can make up for a lack in quality? There may be a place in the world for these types of vendors but you shouldn’t be entrusting the security of your critical applications to mere testing for low-hanging fruit. A comprehensive approach that combines multiple automated tools with expert manual testing is the best way to ensure that your web applications are truly secure.