What is Penetration Testing?

Penetration Testing

Penetration testing can assist organizations in identifying weak points within their infrastructure and demonstrate compliance with industry standards such as HIPAA, PCI DSS or SOX. It also gives peace of mind.

Studies indicate that data breaches can cost businesses millions. Recovering from an attack requires significant financial investments, cutting-edge security precautions and weeks of downtime to recover.

What is penetration testing?

Pen testing (or “pentesting”) involves simulating real-world cyber attacks to identify vulnerabilities and enhance cybersecurity. It can be carried out manually or using automated tools such as penetration testing as a service (PTaaS).

An effective penetration test starts with reconnaissance and scanning to assess the target network and its vulnerabilities, then proceed into planning for its exploitation phase, when testers attempt to gain entry to it.

At this stage, testers must place themselves in the mindset of an attacker by considering their motivation, goals and skills – creating a persona to use when modeling attack scenarios.

After identifying vulnerabilities, penetration testers use various tools to exploit them, including dynamic application security testing (DAST), fuzzing, and static analysis software such as Veracode. Wireshark may also be utilized for network traffic analysis as it captures, decodes and displays data for easy reading – this enables them to uncover hidden or unknown vulnerabilities efficiently and precisely.

What are the types of pen tests?

There’s no one-size-fits-all penetration test – each environment, industry risk and adversary requires different testing techniques. Pen tests may include everything from software flaw identification to physical security weakness assessment – the right test depends entirely on your business infrastructure and systems complexity and scope.

An ethical hacker begins each pen test by conducting reconnaissance, wherein they collect information on the target system to plan their attack simulated attack. Next comes gaining and maintaining access, which often includes different tools or tactics like SQL injections, malware or social engineering to gain and retain it.

Analysis and reporting are the final steps of any penetration test, and will provide valuable actionable insight to help a business identify vulnerabilities and upgrade security measures. It’s recommended that businesses conduct penetration tests at least annually; those with particularly complex infrastructure may require more frequent testing; additionally, penetration tests should be run prior to any significant changes such as new web apps/services being introduced or product releases or mergers/acquisitions taking place in the environment.

1. Open-box pen test

Open-box penetration testing, more commonly referred to as white box or clear box testing, is a comprehensive security evaluation process wherein the pen tester has full transparency into both target systems and networks for evaluation. Testing includes reconnaissance, scanning, exploitation and verification.

Pen testers perform reconnaissance to gather information about the target system by conducting internet searches, social engineering techniques and nonintrusive network scanning. This data helps map out their attack surface and pinpoint vulnerabilities.

Once vulnerabilities have been identified, pen testers utilize tools like Metasploit to simulate real-world attacks on target systems. Once access has been granted, various techniques such as backdoors and rootkits may be employed in order to maintain access and mimic advanced persistent threats (APTs), which remain connected for extended periods in order to steal sensitive data and cause further damage.

Physical penetration tests mimic real-world attacks by breaching physical barriers to gain entry to your business’s infrastructure, buildings, systems or employees. They should be used alongside vulnerability assessments for a more thorough risk-based analysis of its cybersecurity posture.

2. Covert pen test

Pen testing goes beyond vulnerability scanning, which doesn’t give an accurate picture of what’s causing weaknesses and their full impact. Pen testing enables companies to spot gaps in their cybersecurity system so they can close them quickly before breaches lead to costly delays for time, money, and customers alike.

This type of penetration test replicates the actions of criminal hackers without breaching data or company policies. An outside contractor, commonly referred to as an ethical hacker, is employed during this process and will use various means to gain entry into systems; using tools that pierce through cyber defenses while checking for vulnerable spots in networks, web applications, or user security systems.

They then evaluate how far they can penetrate a network or system by identifying and exploiting vulnerabilities, including reconnaissance, gaining entry, burrowing through to systems, maintaining access and extracting desired information/data from them. Some pen tests simulate phishing attacks to assess staff’s ability to keep sensitive information out of cybercriminals’ hands.

3. Closed-box pen test

As cyber attacks become more sophisticated and frequent, businesses must regularly conduct penetration testing of their systems, networks, applications and web security to detect and mitigate cybersecurity risks before they are exploited – helping prevent financial losses, reputational harm and compliance violations.

A penetration test, also known as ethical hacking or white hat hacking, is a legal simulated attack to evaluate the strength of cybersecurity measures and protocols within an organization. Expert hackers conduct these assessments in order to discover vulnerabilities which criminal hackers could exploit in order to access critical business processes or steal sensitive data.

Once information has been gathered during reconnaissance, penetration testers move on to gathering intelligence about the target system by inspecting network traffic and open ports. After gathering this intelligence, they move on to exploiting identified vulnerabilities – usually by burrowing into it further than expected and planting rootkits and backdoors – before producing reports that suggest necessary cybersecurity upgrades.

4. Internal pen test

Pen tests differ from vulnerability scans by replicating actual attacks carried out by real-world threat actors. They include steps such as reconnaissance, gaining/maintaining access, privilege escalation and lateral movement to simulate these potential situations.

Internal penetration testing, often carried out following an external pen test, identifies vulnerabilities which could be exploited by malicious insiders or attackers with access to the network. Furthermore, it simulates how such attacks could harm an organization’s networks, systems and privileged data on-premise or in cloud environments.

Double-blind pen testing (also referred to as zero-knowledge testing) ensures that neither the tester nor target are aware of the scope of a simulated attack, eliminating defensive actions on either party and providing a more accurate representation of potential impact.

5. External pen test

Your business will likely undergo one or more external pen tests as its first penetration tests, with this type focusing on internet-facing systems to identify any vulnerabilities that attackers could exploit to gain entry to applications, networks or sensitive data.

Blind testing allows your organization to be assessed without providing privileged information to testers before beginning its evaluation. This practice simulates how cyber attackers would attack it and is an excellent method for uncovering hidden security risks missed during regular vulnerability scanning processes.

Your business should implement both pen testing and red team assessments as part of its security strategy. By pairing pen tests and red team assessments together, you can identify vulnerabilities in both its infrastructure and policies that may result in security breaches. Contact Pinkerton Investigative Services Team today for more information about how combining these tactics can lower risk while keeping it secure.

Penetration Testing Stages

At this stage of penetration testing, testers use web application attacks such as cross-site scripting and SQL injection to expose vulnerabilities and gain entry. They also attempt to establish persistent presence within an exploited system to simulate advanced persistent threats.

This stage of penetration testing is key because it provides organizations with insight into how bad actors might attack their systems, including tactics, techniques and procedures (TTPs). With this knowledge in hand, companies can identify vulnerabilities more effectively.

1. Planning and reconnaissance

Planning and reconnaissance stages enable pentesters to gather information about the targets of an internal or external penetration test, then use this knowledge as guidance during further phases. For instance, during an external penetration test a tester might use their findings to simulate attacks by malicious actors; they’ll identify host names and IP addresses, perform vulnerability scanning, and uncover ways to gain entry to assets targeted in this way.

According to the EC-Council, recon phases often include techniques like DNS interrogation, network sniffing and banner grabbing to gain insights into network systems. With this knowledge in hand, hackers are then able to attack these networks by increasing privileges or stealing data or intercepting traffic – potentially leading to successful attacks against these vulnerable networks.

This stage of penetration testing, often called “gaining access,” sees testers exploit any vulnerabilities found during discovery and reconnaissance phases by exploiting any vulnerable points using tools such as Metasploit designed to mimic real-world attacks.

2. Scanning

Scanning is the second stage of penetration testing, where pen testers utilize tools to assess systems for potential vulnerabilities. This phase can involve active hacking techniques such as SQL injection, cross-site scripting and other web application attacks; as well as passively gathering intelligence using open-source intelligence (OSINT).

Scan tests allow pen testers to discover weak passwords and other security flaws within systems in order to gain unwarranted entry and exploit them in order to exploit or gain unauthorised access to them. This may allow an attacker to escalate privileges on compromised systems to gain access to confidential data or assets that could prove valuable for an attack.

Another essential part of this step is maintaining access, with pen testers striving to replicate the persistent behaviors of cybercriminals by remaining undetected as long as possible – this also provides invaluable insight into real attacks, which helps shape improvements for cybersecurity improvements.

3. Gaining Access

Exploiting, the final stage in penetration testing, requires ethical hackers to use information gleaned during reconnaissance and discovery to attack and breach a targeted network using tools such as Cobalt Strike or Metasploit to identify vulnerabilities. This stage simulates what bad actors might do to your technology by encrypting data, exfiltrating sensitive information or even taking over systems demanding ransom payments.

Exploitation also assists testers in locating sensitive internal data and determining how they could gain access to more systems within your network. When penetration testers reach their objective of their attack, they report their findings and offer solutions for remediating issues found during the simulated hack; usually this information will be included in a detailed report that includes vulnerabilities discovered and data that was compromised.

4. Maintaining access

At this step, penetration testers evaluate the overall security of a target system by employing automated tools to probe for vulnerabilities. This includes investigating network infrastructure like servers, host ports and services that might be vulnerable to breach.

Pen testers typically spend the bulk of their time during this stage attempting to gain entry to target systems using various toolkits and attacks like social engineering and code injection to gain entry and exploit weaknesses, according to EC-Council. The process requires patience in order to effectively probe for possible entryways into them.

Penetration testers also utilize various tactics to replicate real-life threat actors by simulating theft or lockdown and ransom demands, helping demonstrate whether vulnerabilities could be exploited by adversaries in the wild. Once this phase is completed, penetration testers create an exhaustive report detailing all methods they employed in uncovering software vulnerabilities as well as their consequences.

5. Analysis

Once the penetration testing team has finished their work, it is time to analyze their findings. At this stage, a report should be produced which details each phase and asset tested; type of pen test employed; vulnerabilities found and their consequences; as well as remediation guides or plans that should be included within this document.

This analysis can help you quickly identify and prioritize vulnerabilities based on CVSS scores – used to rank vulnerabilities according to criticality. You can then use this data to plan remediation strategies accordingly. Once the pentest is over, penetration testers should also ensure they clean up the environment they breached as part of their test, including disabling any new access they created, reconfiguring access rights or making other necessary changes that they made; doing this helps prevent any potential damage or interruptions to business operations.

Final Thoughts

Penetration testing is a form of security assessment designed to identify and prioritize vulnerabilities within IT infrastructures. Penetration tests are typically carried out by ethical hackers who conduct simulation attacks against servers, endpoints, networks, web apps, or any other potential points of vulnerability in order to expose these flaws and assess them appropriately.

GRC processes include conducting periodic pen tests as part of their GRC processes to detect ways hackers might gain entry to your systems and cause data breaches, which can be costly and damaging to both reputation and costs. Pen tests also serve as a framework for assessing overall risk; by rating risks you can take measures to address them more efficiently while making better IT investment decisions.

Penetration testing is an integral component of any effective cybersecurity system. It gives invaluable insights into how hackers might target your systems, providing a blueprint for mitigating risk exposure. No security system is 100% foolproof so regular penetration tests should be carried out to identify and address any vulnerabilities promptly.

Sam is an experienced information security specialist who works with enterprises to mature and improve their enterprise security programs. Previously, he worked as a security news reporter.