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It’s time to go on the cyber security offensive!

Leverage automated penetration testing to detect system vulnerabilities faster than attackers

14 May 2024Dheeraj Rawal

The backdrop

Waiting for a cyber attack to expose vulnerabilities in your systems is akin to playing with fire. Organizations cannot risk taking that approach anymore. They can go on the offensive with penetration testing. In this blog, find out how penetration testing can serve an organization’s interest in ramping up security measures. How businesses can gain speed and scale with automated penetration testing, and anecdotes of companies that could have avoided costly data breaches. 

Penetration testing: A proactive approach to security

As the attack surface grows and organizations are plagued with cyber attacks, the demand for penetration testing (also known as pen testing and ethical hacking) is undoubtedly growing. Penetration testing isn’t a new phenomenon. In 1967, about 15,000 security experts and other professionals gathered in a conference to discuss whether communication lines could be penetrated.1

In a way, this was the beginning of the penetration testing process – where security teams would orchestrate attacks on their infrastructure to find out security vulnerabilities in systems, networks, hardware, software, etc. Although the methodologies have advanced, the goal is to fill the security gaps and improve the security posture.

Organizations realize that many of these cyber attacks or data breaches are outcomes of attackers exploiting an existing vulnerability or more in the system. However, they only comprehend this in hindsight after an attack has already taken place. Naturally, pen testing is a good proactive approach to identify weaknesses in the system before any security incident or data breach.

Vulnerabilities that turn out to be too expensive

Data breaches are becoming commonplace. In 2023, more than 8 billion records were breached in about 2,800 security incidents.2 Data breaches can cost organizations a lot of money. The average cost of a data breach stood at $4.45 million in 2023.3 Can data breaches be avoided with offensive security approaches such as penetration testing? By all means, yes. 

Some of the common reasons for data breaches are weak and broken authentication, unpatched software, misconfigured services and applications, insecure APIs, etc. With penetration testing, these problems can be identified in advance. Issues such as weak authentication and broken access may seem insignificant, but they can cause catastrophic damage.

Stories of vulnerabilities that caused severe attacks

In 2019, First American Financial Corporation, a US-based finance services company, faced a data breach in which about 885 million sensitive documents were exposed.4 These documents were related to customers’ bank account numbers, statements, mortgage records, and so on. 

All these documents were stored on the company’s website page and intended to be accessed by specific users. However, anyone who managed to get to the link of this webpage could get their hands on this sensitive customer data. This is a simple case of an authentication problem, which was exploited. In 2023, the company reached a $1 million settlement with the New York State Department of Financial Services (DFS).

Equifax, another US-based credit reporting agency, suffered a data breach in 2017 due to a web portal vulnerability, which cost them $1.4 billion in settlements. Read more about it here.

To cut to the chase, penetration testing tools could have detected security vulnerabilities early on and prevented the damaging outcomes. 

How does penetration testing work?

Pen testing is usually carried out by the security team in a phased manner, as explained below:

  1. Planning & reconnaissance: Understanding the objective of the pen testing – which systems need to be targeted, what security tools need to be used, etc.
  2. Scanning: Scanning systems and networks to identify vulnerabilities.
  3. Gaining access: Exploiting one or more vulnerabilities to get into the system.
  4. Maintaining access: Attempting to remain undetected in the system.
  5. Analysis & reporting: Analyzing weaknesses in the systems, how they can be exploited, and other details.

Apart from identifying weaknesses, organizations conduct pen testing for several other reasons, such as to assess the effectiveness of the existing security controls, to meet compliance requirements, and to manage and mitigate cyber security risks. It builds confidence amongst stakeholders and customers. 

Understanding the scope of penetration testing

Penetration testing is different from vulnerability assessment. Vulnerability assessment aims just to identify weaknesses in the systems, while penetration testing aims to exploit these weaknesses and gauge the impact of the attack and the effectiveness of the security controls.

Pen testing is performed to assess different systems such as networks, web applications, APIs, wireless networks, social engineering (to check vulnerabilities in human behavior), physical penetration, red team (full-fledged real-world attack simulation), and so on. 

These systems are tested by launching attacks both from outside and inside of the organization. Depending on what access and information is given to the penetration tester, there are three categories.

Types of penetration testing

Infographic displays different types of penetration testing
  1. White box testing 
    This type of testing is carried out to determine vulnerabilities from an insider’s view. It determines how anyone with access to internal systems can potentially cause damage. It uncovers vulnerabilities such as coding errors, insecure configurations, internal network structure, etc. 
  2. Black box testing
    Close to a real-world cyber attack, this is launched externally from the attacker’s perspective where no access or system-related information is shared with the tester. Through black box testing, testers can find vulnerabilities related to injection attacks, DDoS, web application problems, server misconfiguration, authentication, and broken access control, and so on. 
    For instance, broken access control isn’t an uncommon problem. In 2021, OWASP reported that 94% of applications that were tested had broken access control issues.5 Due to broken access control, users may see the information they aren’t supposed to see. There are other implications such as unauthorized access, privilege escalation, data leakage, non-compliance, and more. 
    In Equifax’s data breach case, the web portal vulnerability was exploited. About 143 million people were impacted by this data breach. Such existing vulnerabilities can be identified with penetration testing. In this specific case, black box testing can be fruitful.
  3. Grey box testing
    In this type, the tester is given some information about the systems. With this partial knowledge, the tester can try to find vulnerabilities not just at the coding level, but also at the functionality level – striking a balance between white and black box testing. 

However, there are certain challenges with manual penetration testing.

The downsides of manual penetration testing

  1. Time-consuming: Security posture assessments and in-depth manual validations could take several months in some cases.
  2. Resource-intensive: Organizations require skilled professionals, the right tools, and a budget. 
  3. Error-prone: Manual pen testing is susceptible to errors because security teams may inadvertently overlook some vulnerabilities. The manual approach also generates many false positives and false negatives.
  4. Limited coverage: Not all systems or attack surfaces are covered because testers don’t test what they don’t know or see, sometimes missing out on carrying pen testing in-depth.
  5. Inconsistent: Professionals use different methods resulting in outcomes that may not fully reflect the status quo of the vulnerabilities and security posture.
  6. Non-scalable: For organizations that are growing with modern continuous integration/continuous deployment (CI/CD) strategies, manual penetration testing is difficult to scale with limited resources.
  7. Skill availability: Due to the complexity of the testing, not many high-skilled pen testers are available in the market, creating a skill shortage.
  8. Costs: Most organizations need external professionals and tools to carry out comprehensive penetration activities. Due to skill shortage, the professionals in demand command high prices, which makes this a costly affair.

These downsides of manual penetration testing encourage businesses to opt for automated penetration testing. 

What’s automated penetrating testing?

Programmer working with computers

In the automated pen testing approach, organizations rely on the use of advanced tools rather than human intervention to identify vulnerabilities within the organization’s network, applications, or systems. Any business, regardless of scale, with a digital landscape and attack surface can use this automated approach to put up proactive cyber defense.

Automated pen testing makes a compelling case for its adoption. It streamlines the processes and allows faster execution of the testing process, cutting down the timeframe of the project. This is one of the key features, because repetitive and time-consuming tasks can be automated with the workflows. It can mimic an array of attack scenarios to speed up the testing process.

More benefits of automated penetration testing

It also enables repeatability so that organizations can go through routine assessments. The ability to scan and monitor continuously allows organizations to discover new weaknesses, outdated/unpatched applications, misconfigurations, weak authentication, incorrect access controls, and so on. These can be fixed to ensure minimal disruptions and business continuity. Organizations can also gather insights through detailed analysis and reporting capabilities. The reports also generate a system risk profile by ranking vulnerabilities according to their severity. 

Organizations can deploy automated penetration testing across large infrastructures without worrying about scalability and coverage issues. This testing approach is also a cost-effective alternative because businesses don’t need to invest a lot of time and money in hiring skilled security testers. 

While automated penetration testing doesn’t eliminate the need for human intervention altogether, the efforts needed is lesser, allowing security teams to focus on other critical functions. 

How does automated penetration testing work?

Reconnaissance: Automated tools gather information about the target network, systems, applications, entry points, and vulnerabilities.

Scanning: Scanners are systematically deployed to probe the target environment for open ports, services, and vulnerabilities.

Enumeration: Automated tools compute system details, such as user accounts, network shares, and configurations, to further refine the scope of potential exploits.

Exploitation: Scripts are deployed to exploit vulnerabilities and gain unauthorized access, execute commands, and manipulate system resources, mimicking real-world attack scenarios.

Post-exploitation: Continuation of gathering information, escalating privileges, and maintaining access to compromised systems.

Reporting: Detailed report generation of findings from the automated pen testing. This report also includes severity, recommendations for remediation, and prioritization.

All these phases are carried out with the help of automated tools. These tools offer a framework for developing, testing, and executing exploits against the target systems. Some of these tools also have a vast database of known vulnerabilities, making automated pen testing very effective. They can detect weaknesses in SQL injections, cross-site scripting (XSS), server misconfigurations, etc.

Some of the popular tools for automated penetration testing in the market are RidgeBot, Metasploit, Nessus, OpenVas, Burp Suite, Armitage, Nmap, SQL Map, ZAP, and more.

Businesses are shifting towards automated pen testing to proactively identify vulnerabilities in their systems and mitigate the risks of cyber attacks and data breaches. They want to improve security posture, enhance compliance rates, and protect data with offensive security strategies. Damages such as financial and reputational losses and legal liabilities can be avoided through such security approaches.

Find vulnerabilities through automated penetration testing with T-Systems

With demonstrated experience and expertise, we can conduct comprehensive network and web application penetration testing. Post-testing, we offer a technical and executive report with our recommendations that help you prioritize the next steps. Our security experts are Offensive Security Certified Professionals (OSCP) and they adhere to best industry practices and regulatory frameworks. We also follow the MITRE ATT&CK framework for standardization, mapping, in-threat emulation, risk assessment, and continuous improvement.

Build confidence in offensive cyber security strategy with us. Begin a conversation with us to know more.

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About the author
Dheeraj Rawal

Dheeraj Rawal

Content Marketer, T-Systems International GmbH

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1 The History Of Penetration Testing, 2019, Infosec Institute
2 List Of Data Breaches, 2024, IT Governance
3 Cost Of Data Breach, 2023, IBM
4 First American Financial Data Leak Article, 2019, Forbes
5 Broken Access Control Report, 2021, OWASP

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