What Is Penetration Testing and Why You Need To Do It

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What is Penetration Testing in Cybersecurity?

Penetration testing, or pentesting, in cybersecurity is like hiring an experienced burglar to break into your home and attempt to steal your jewelry after you have established all of your home’s security systems. In cybersecurity, pentesting is an exercise where security researchers called ethical hackers perform a simulated cyberattack on an organization. The goal is to probe the organization’s network and applications for vulnerabilities that could be exploited by a cybercriminal.

It is the closest you can get to a real world attack without suffering any of the negative consequences. Results of pentesting can be used to fix or otherwise address problems before they can be used to compromise the system. A thorough pentest includes post-test analysis that can identify any security measures, including weak or ineffective policies or controls, that should be updated or improved. 

Why Do I Need to Pentest?

Cybersecurity breaches show no sign of slowing down, and they are becoming more expensive to organizations. The average cost of a data breach worldwide increased to $4.35 million in 2022. In addition to the monetary impact, breached organizations can experience reputational and legal consequences as well. Breached organizations are all over the world and in many diverse business sectors.  A few high profile breaches in 2022 were the Costa Rica Government breach where thieves stole high-value data and held it for ransom, the Neopets gaming breach where thieves stole 69 million user records and posted the personal information for sale on an online forum, and the Uber breach where thieves gained access to 57 million user accounts. 

These statistics make it clear that building a strong cyber defense should be top priority. But how do you know that your computer systems and applications are secure? The best way to find out is to hire an experienced security team to try to penetrate those defenses. 

What is a Pentester?

A pentester is an experienced and trusted security professional with knowledge both in the nature and application of cybersecurity systems and how to circumvent those systems. Often these ethical hackers have worked for cybersecurity software companies or agencies. Sometimes they are reformed criminal hackers who now work to help organizations defend against attacks. Synack pentesters comprise the Synack Red Team, a global community of 1,500+ security researchers who have been put through a rigorous vetting process before they are allowed to participate in pentesting programs.

What are the Types of Pentesting?

There are several ways to describe the different types of pentesting. Two of the more useful are manual vs. automatic testing, and the type of access given to the pentesters.

Manual vs. Automated Pentesting

Automated pentesting uses a predetermined set of tests to attempt to penetrate cyber defenses. These tools are often based on known sets of vulnerabilities such as the OWASP Top 10. Automated testing produces results quickly and does not require large teams of experienced professionals. This type of testing is good for testing against known vulnerabilities and for providing an overall estimate of cybersecurity posture. 

Manual pentesting allows pentesters to use human ingenuity to attempt to breach cyber defenses. They can think like an attacker, analyze penetration activity and adjust their strategies. They can also assess what damage can be caused by a successful breach, including any ability to move laterally through the system. Synack performs both scanning and in-depth, human-led pentesting and then follows up with remediation assistance and verification.

Access to Systems

One of the preliminary decisions to be made in planning for a pentest is what access and information the pentesters will be given. In a black-box type test, pentesters are not given any access to or information regarding the system to be hacked other than what can be found in public sources. This will produce a scenario that is the closest thing to a real world attack. Testers may be given a specific goal, e.g. see if you can steal this proprietary data, or they may be free to root around to see what damage they could do. 

In a white-box type test, testers are given credentials to gain some level of access to the system.  They won’t have to spend time trying to break into the system, so they can concentrate on analyzing internal security structures and processes. In white-box testing testers usually have full access to the system. In grey-box testing, testers are given only partial access, such as low level or limited credentials. Since the tester has access credentials, this type of testing can also be used to simulate an inside job, where an employee or vendor perpetrates the attack.

What is the Difference Between Pentesting and Vulnerability Assessment?

Vulnerability assessments are related to but different from pentesting. A vulnerability assessment searches for known vulnerabilities in a system. The assessment is typically performed with automated tools and is, therefore, relatively quick and inexpensive compared to manual pentesting. It produces a report with suggested remediation steps, but does not attempt to exploit the security vulnerability nor analyze how damaging the exploit would be to the organization.

In the home analogy, a vulnerability assessment is like checking all of the known entries to your house and the safe where your jewelry is kept to make sure they are locked and alarm systems are armed. But it doesn’t turn a burglar loose to see if he can find ways to break in. He might find a faulty crawl space screen, or he might disguise himself as a workman to gain access to the house. If you run a vulnerability assessment to help gain an overall picture of cybersecurity posture, you should follow it up with a full manual penetration test.

How to Pentest my System?

A comprehensive pentest requires planning and follow-up in addition to the actual penetration attempts.  

Planning: The organization needs to determine the goal of the test. The goal might be simply to see if a hacker can break into the system, or to see how many exploitable vulnerabilities can be discovered. Or, there could be a specific goal like seeing if a hacker can steal some particular sensitive information. The organization also needs to determine how the attack will be carried out. Will it be a white-box or black-box test? Will IT be aware of the attack in progress and how are they to respond?

Reconnaissance: Once the goal has been established, pentesters will gather as much information as they can about the target and its attack surface. Then they will map out a preliminary strategy.

Gaining Access: Testers examine all possible entries into the system and determine the best tools to use. They might use malware or social engineering. Numerous software tools are available for hackers, including those designed to produce brute-force attacks or SQL injections.

Maintaining Access: Once testers gain access to the system, they need to proceed stealthily, maintaining access long enough to achieve their objective. They might try to move deeper or laterally through the system to see how much access they can gain.

Reporting and Remediation: After pentesting concludes, testers should provide a detailed report, in language that the organization stakeholders can understand, on each test with results as well as suggested remediation steps.

Verification: A comprehensive pentesting effort is not over until all remediation steps have been verified as implemented and working successfully.

How Often Should I Pentest?

Security experts recommend performing pentesting on a regular basis to respond to emerging vulnerabilities. The frequency of testing depends on the organization’s size, business, and security requirements. Large organizations are ripe targets for attack and need to be continually vigilant. Organizations dealing with regulations often need to follow testing mandates. All organizations should conduct pentesting after any infrastructure changes such as patch installations, security policy modifications, hardware and software upgrades, and after opening new facilities or locations. Synack offers an on-demand security testing platform, enabling continuous pentesting for maximum protection against attacks.

Learn More About Penetration Testing

For more information about penetration testing and how Synack can help your organization protect against cyberattacks, go to www.synack.com

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