Unfortunately, software companies are ideal targets for cyberattacks—with the ever-evolving nature of these organizations and their IT infrastructure, they are often left vulnerable. With the rapid growth of software companies comes the mirrored growth of their attack surface, and consequentially the rapid growth of vulnerabilities. While traditional pentests may cover you for a few weeks, Continuous Penetration Testing (CPT) secures organizations’ data, well... continuously. As your attack surface changes, CPT picks up on vulnerabilities and gives you the steps to remediate—not once a year, but as they come up.
The Living Nature of Software
Software is a living, breathing industry. In turn, you need to have a living, breathing security strategy. Traditional pentesting models are static—they don’t grow as you grow or catch vulnerabilities as your attack surface changes. These pentests take around 20 days to complete. That means that your organization is essentially left vulnerable for the remaining 345 days of the year. And with the software industry specifically, where code changes and your attack surface shifts constantly, 345 days of vulnerability is not only less than ideal, but it could also potentially be disastrous.
The Problem with Static Security: Trustwave and Target, 2013
All the way back in 2013, Target (and their credit card security vendor, Trustwave) faced a lawsuit from two major banks following a data breach that allowed for 40 million payment card records to be leaked. The allegation? Target and Trustwave failed to properly secure customer data. Not only was credit card info stolen, but 70 million other records (including phone numbers and addresses) were breached as well. The banks lost millions, having to reimburse fraudulent transactions and reissue cards.
The issue reached the U.S. Senate, where it was said that Target “missed a number of opportunities to stop the breach.” According to the suit, Trustwave boasted “deep expertise” in payment card industry compliance, despite failing to find any vulnerabilities right before the breach occurred.
In this case, several issues came up— Trustwave had completed a pentest report back in September of 2013 (the breach happened from late November to early December) and had incorrectly identified zero vulnerabilities. Not only had they missed the initial vulnerability, but the breach also continued for nearly three weeks, all under Trustwave’s watch. This also brought in the subject of compliance—Trustwave, and therefore Target, were not compliant with industry security standards, thus exacerbating the risk.
Continuous pentesting wasn't a recognized methodology all the way back in 2013, but had Target employed a more preventative, proactive approach, this could have been avoided. Not only to stay compliant, but to catch vulnerabilities as they come up and take steps toward remediation.
What Continuous Pentesting Offers
The issue that we saw with Trustwave and Target came down to a lack of proactive security, plain and simple. Now that we’ve broken down why this doesn’t work for Software companies, let’s go into what continuous testing can do for you:
- Constant awareness and visibility – as your attack surface changes, continuous testing models allow you constant visibility into what vulnerabilities may be lurking. This is instrumental in taking quick and efficient steps toward remediation.
- Real-time, actionable insights—security is not a “one and done” kind of thing, as we explored with Trustedwave/Target’s lawsuit. With continuous penetration testing, you’re getting insight into what vulnerabilities are popping up, AS they pop up. The security experts behind the tests can give you actionable steps to take to remediate, allowing you to stay ahead of the curve, and ahead of the breach.
- Built for fast-moving development—this is instrumental for the software industry. Software is constantly changing and evolving, which means new vulnerabilities are constantly being added and discovered. With a fast-moving infrastructure, you need fast-moving security. As software companies grow, their environment becomes more complex. CPT scales alongside that growth. It evolves with your tech and your team. Much like a living immune system, CPT allows you to adapt to new threats, not just “reboot” once a year.
Why This Matters NOW
In today’s ever-evolving security world, the cost of a breach is higher than ever. Not just financially—but legally, and reputationally. We operate in a society of trust. Trust that the companies we give our information to are keeping it safe. Trust that our livelihood won’t be impacted by the recklessness of those that we give our money to. When that trust is breached, there’s really no way to gain it back.
As the tech and security landscape changes, attackers are using AI, automation, and ever-evolving tactics to steal data. If your defenses aren’t evolving too, you’re falling behind. CPT helps you stay one step ahead—detecting what others miss and adapting as you grow.
Conclusion – Make Security Part of the Living System
When an industry like software operates as almost a living, breathing organism—security needs to be part of its DNA. Continuous Penetration Testing moves, learns, and grows alongside your product and your organization. Don’t treat your security as some static object. Treat it like a living organism that needs ongoing care.
