Security | Threat Detection | Cyberattacks | DevSecOps | Compliance

Most teams approach network penetration testing the same way: pick a few well-known tools, run automated scans, and call it a day. But in today’s evolving threat landscape, that is a losing strategy. Attackers do not just rely on off-the-shelf exploits but adapt, chain vulnerabilities, and find gaps that automated tools miss. CTOs and engineering leaders need to rethink their approach with respect to context, strategy, and how they integrate into your security workflow.

The history of penetration testing begins with military strategies used to test enemy defenses. Over time, this evolved into a formal practice for identifying vulnerabilities in computer systems. This article traces the brief history of of penetration testing, from its early conceptual roots in military exercises, through the rise of ‘Tiger Teams’ in the 1970s, to the sophisticated tools and methodologies in use today.

When was the last time your business or enterprise tested its defenses with a real-world attack simulation? If the answer is never—or more than a year ago—your company may be more vulnerable than you think. Regular penetration testing by an expert team like Cybriant is one of the most effective ways to uncover and fix security weaknesses before attackers exploit them. Interested in learning more? Read on.

Imagine a bridge built without stress testing, where engineers only check for cracks after construction. When flaws inevitably appear, they scramble to patch weak spots until the subsequent failure forces another round of inspections. This is how most companies still approach pentesting: periodic assessments, reactive fixes, and security are treated as unwelcome checkpoints.

Most teams approach network penetration testing the same way: pick a few well-known tools, run automated scans, and call it a day. But in today’s evolving threat landscape, that is a losing strategy. Attackers do not just rely on off-the-shelf exploits but adapt, chain vulnerabilities, and find gaps that automated tools miss. CTOs and engineering leaders need to rethink their approach with respect to context, strategy, and how they integrate into your security workflow.

AI is reshaping industries, but security teams treat it like traditional software. Unfortunately, the real problem is AI models don’t just have bugs—they have systemic vulnerabilities. Adversarial manipulation, data poisoning, and model inversion aren’t edge cases; they’re real threats attackers are already exploiting. Yet, most security programs lack a structured approach to testing AI risks. Conventional pentesting isn’t enough.

A critical aspect of manufacturing, energy, and transportation is Industrial Control Systems (ICS) and Operational Technologies (OT). The rapid pace of digital growth makes these systems susceptible to cyberattacks. OT and ICS system security is important, making penetration testing an essential activity. This tactic makes it possible to mitigate weaknesses so they are no longer vulnerabilities. It is an effective measure of asset protection.

Cyberattacks don’t usually begin with sophisticated hacking techniques. Often, they start with something far simpler—stolen credentials. A phishing attack, a leaked database, or even weak internal security controls can provide an attacker with legitimate access to an organization's network.

Threat-led penetration testing brings together specialist offensive (red team) security skills and threat intelligence to enable businesses to proactively test and identify any weaknesses, deficiencies or gaps in their controls and counteractive measures that could be exploited by threat actors. In this article, we set out what threat-led pen testing is, how it relates to the Digital Operational Resilience Act (DORA) and the testing requirements included as part of the new EU regulation.