Why digital transformation needs more flexible security testing

Whether it’s a global enterprise redefining a business process using cloud computing and machine learning or a sole trader setting up a social media presence for the first time, digital technologies continue to change and, for the most part, improve the way organisations operate. They are now part and parcel of the quest for efficiency, innovation, and agility that drive transformation projects everywhere. And, despite widely expressed concerns about potential misuse, AI’s ability to analyse and process vast tracts of data is set to be an even greater catalyst for the creation of new business models and ways of working.

However, for all the advances and benefits, there has been a price to pay in terms of cybersecurity risks, which have grown in tandem. Attack surfaces have expanded rapidly, and data volumes have rocketed with much of it in large, unstructured formats. Agility has brought its problems, too, as the speed of digital transformation has, at times, outstripped security measures. This has led to the rushed adoption of technology and pressure to bring new products to market before sufficient testing has been completed.

The vast amount of sensitive data generated, shared, and stored in sprawling digital ecosystems has become a lucrative target for cybercriminals. However, ensuring the security of these systems, which often stitch together legacy and new technologies, is constantly undermined by the shortage of security professionals and resources.

As a consequence, any weaknesses have been readily exploited by malicious actors, employing a raft of tools and techniques that are continuously being updated and weaponised with different tactics.

In turn, vendors have retaliated with an ever-growing array of options to prevent, detect and respond to threats, increasingly relying on automated vulnerability scanning and machine learning to augment the shortage of skilled security analysts. 

Ensuring that cyber security defences are keeping pace with the threat landscape as well as the demands of digital transformation, whether from day-to-day modifications or large-scale projects, is a relentless challenge. To stay abreast of changes requires non-stop attention, which is where external pen testing can help take the weight off internal teams.

Through the eyes of a hacker

Often perceived as a solution only appropriate for a finite testing period before launching new software, applications, or systems, modern pentesting or “PTaaS” now enables faster and more flexible testing regimes. Using a combination of tools and human intelligence, tests can cover large environments or focus on a particular aspect, such as web applications, wireless networks, physical infrastructure, social engineering, or mobile apps.

Taking on the ruthless mindset of malicious actors with their eyes fixated on the prize, ethical hackers will try to break into whatever a customer specifies. Their deep understanding of programming languages and network protocols means they can simulate exploits and payloads. Having gained unauthorised access, the next goal is to discover the easiest route to escalate privileges to reach sensitive data. Ethical hackers excel at critical thinking and creative problem-solving as attacks may not unfold as expected, so they must react quickly to different problems or opportunities as they arise.

Customers benefit from being able to call upon an extensive range of skill sets and expertise that they would not be able to maintain in-house.  Upwards of hundreds of thousands of registered testers are available at any given time from crowdsourced ethical hacking providers, offering continuous and dynamic testing with the capability to scale up or down as required. Registered hackers undergo rigorous vetting, including skills evaluation, identity verification, and their adherence to ethical standards, ensuring a high level of trust and competence. The procedure involves simulated challenges in real-world scenarios to assess the hacker’s ability to uncover vulnerabilities efficiently and responsibly.

Testing teams can be made up of different skill sets to ensure comprehensive expertise is applied at the volume and velocity required.  Final reports provide detailed findings covering vulnerabilities, compliance implications, and recommended remediation steps.

Pentesting as part of a security strategy

Penetration testing is a necessary part of evaluating the strength of cyber defences. The benefits of pentesting are well noted, with a 54% increase in this security exercise since last year. As a result, 16% more vulnerabilities surfaced year-on-year. However, too many organisations are sidelining assessments instead of making them an integral part of development workflows and security programs. In a traditional model, a product is developed, and a pentest is conducted at the completion of development to check for vulnerabilities. Any issues are patched at this point and re-tested until a fix is effective. These multiple cycles of testing and patching at such a late stage slow down releases and add on avoidable costs.

With a modern approach, testing occurs throughout the development cycle. Testing can now begin within days, not weeks, issues can be highlighted and corrected before they cause further problems down the line, which reduces the need for patching at the end. Moreover, knowledge transfer across IT security teams and developers helps to improve future coding, minimising security flaws and reducing the need for last-minute remediation.

Penetration testing results can also play a crucial role in shaping future cybersecurity strategies by providing organisations with actionable insights into their security posture. These tests uncover weaknesses and potential points of exploitation across multiple systems and applications. Consolidating findings not only allows security teams to prioritise and address the most immediate issues it also enables organisations to review their security strengths and weaknesses within different areas of their business.

If organisations infuse old-style vulnerability scanning and pentesting with new, independent thinking, they will gain deeper insights into the tactics of their adversaries. Using the feedback gathered can guide the creation and enhancement of security policies as well as product development workflows and cycles. Following this iterative process will contribute to a more resilient and adaptive cybersecurity posture that improves the efficacy of technology-driven business initiatives and better supports the changing demands of digital transformation.

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Chris Dickens
Senior Solutions Engineer at HackerOne | + posts

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