Corporate Cybersecurity. John Jackson

Acknowledgments

      There are far too many influential people in my career to mention in this section. I’m thankful for all of the information security individuals who have let me learn alongside them, given me opportunities, and have put my skills to the test. I’ve learned many lessons along the way.

      A special thank-you to my friend Christian Bobadilla is in order. Christian is one of the most talented application security experts I know, and his humility keeps him out of the information security limelight. Through me, your excellent advice and mentoring lives. If it weren’t for you, I wouldn’t know even a quarter of what I do about bug bounty programs. Thank you for being a positive role model in my life. It’s exceedingly difficult to find people who are not only intellectually sharp and humble but also incredible leaders. This book is dedicated to the faith that you have put in my abilities.

      One final dedication: to my father, who encouraged me to try my best at all times. Rest in peace.

Part 1 Bug Bounty Overview

1 The Evolution of Bug Bounty Programs

      1.1 Making History

      Understanding the evolution of bug bounty programs first requires familiarity with the hacking landscape, or as many in the information security field know it, penetration testing. Security researchers haven’t always been respected or given the opportunity to shine. Throughout history, hacking has been a word that scares the public and creates waves of fear inside a company when rumors of a “hack” spread. The first bounty paid for breaking into something (in recorded history) was in 1851. Charles Alfred Hobbs was paid roughly the equivalent of $20,000 to pick a physical lock. (https://www.itspmagazine.com/itsp-chronicles/history-and-interesting-facts-about-bug-bounties-an-appsec-usa-2017-panel-recap).

      The first actual bounty program was run by Netscape and it began in 1995. The primary scope was application testing for Netscape Navigator 2.0., their primary product. Slowly, other enterprises started to adapt their own bug bounty programs and offer awards. Bug bounty crowdsourcing platforms introduced the new wave, compiling enterprise programs into a neat catalogue in which security researchers could hop into various programs and begin to participate. Bugcrowd was known as the first crowdsourcing platform in bug bounty history and has been a key player in enterprise bug bounty program management. The pioneers – Casey Ellis, Chris Raethke, and Sergei Belokamen – believed in connecting latent potential to unmet demand with the overall goal of making security easier for everyone. In addition, Ellis firmly believed in assisting security researchers in keeping their records clean. Casey Ellis has also expressed a desire to help educate the youth toward the idea of ethical hacking, rather than a life of crime, and part of the inspiration for creating such a company has to do with the ideal of destigmatizing security research.

In all actuality, reviewing the state and history of bug bounty programs gives the reader a valuable positive perspective, but enterprises are slow to adapt. Even since 1995, there are still fewer than 400 bug bounty programs and 1600 vulnerability disclosure programs that exist in the world. The surprisingly small number of programs that exist in the world represent the resistance and conservatism of the field of legal hacking, otherwise known as security research.

      1.2 Conservative Blockers

      When information security specialists learn about bug bounty programs, many of them are excited to get involved. Application security is a growing field, and modern day web, mobile, and hardware assets need to be protected. With such an essential requirement to protect applications, enterprises still resist the absolute necessity of making vulnerability reporting management a prioritized incentive. As with everything, there’s not a “one-size-fits-all” answer for why an enterprise would ignore application security; however, many factors play a role in the resistance that is widespread, even today. For example, here are some of the reasons a company may decide to ignore the idea of a bug bounty program:

       Increased threat actor activity.

       Security researchers scamming.

       Applications being a small consideration.

       Enormous budgetary requirements.

       Other security tooling as a priority.

      There are obviously several other reasons an enterprise may believe a bug bounty program will cause unnecessary risk or negative effects. Debunking the above five defined points will give people a better understanding of why being afraid is natural, but it can be detrimental to the overall health of a good application security program.

      1.3 Increased Threat Actor Activity

      An enterprise may be fearful that establishing a bug bounty program will cause an increase of malicious threat actors attempting to hack into or successfully exploiting applications. The logic can be portrayed as such, “If an enterprise bug bounty program is established, then security researchers will be allowed to hack, and it will be impossible to tell who is malicious.” The problem with this statement’s assumption that threat actors are hiding among security researchers is one of a common philosophical logical fallacy: the Slippery Slope.

      The Slippery Slope logical fallacy is best defined as, “A course of action that seems to lead inevitably from one action or result in another with unintended consequences.” In layman’s terms, the translation of the Slippery Slope in the security research scenario is, “If the enterprise allows security researchers to conduct research, we will be maliciously exploited.” It’s best to imagine the scenario of increased threat actor activity with the other perspective in mind. Without a bug bounty program, flaws may never be identified – vulnerabilities that could compromise an organization’s sensitive information or intellectual property.

Enterprises considering operating bug bounty programs should learn effective logging and prevention through logging mechanisms and web application firewalls, which are discussed later in this book.

      1.4 Security Researcher Scams

      Any type of business that relies on services rendered by another party should always be weary of scamming. Understanding the vulnerability types, criticality, and assessing payment amounts will always be the best course of action for a company running a bug bounty program. Still, the idea of scamming isn’t a new one. Potential program managers have to learn best practices and understand the basics of vulnerability management. Nonetheless, protections for programs are in place. Managed services offered through bug bounty crowdsourcing platforms such as Bugcrowd and HackerOne will become useful tools. The triage team will assist in validating the legitimacy of a vulnerability which can assist in preventing scamming. Program managers shouldn’t solely rely on the validation, but scamming happens far more infrequently than enterprises that are on the fence imagine.

      1.5 Applications Are a Small Consideration

      Enterprises that avoid bug bounty programs because of the idea of applications being a small attack surface are asking for trouble. When employees tasked with the security of a company evaluate vulnerability potential, the obvious go-to is to secure the network and related assets. However, web and mobile applications in particular have become exceedingly complex. With multiple development languages and servers, the attack surface is far greater than one might imagine. Consider the following example:

      Server → Hosts one part of the web application → One assigned IP address

      Web application → Connected to multiple servers → Multiple IP addresses

      The deployment of an enterprise’s assets will always be the determinant factor in the