When Is Pen Testing Most Effective?


Penetration testing is valuable for any organization with serious cybersecurity concerns. It uncovers problems that would otherwise go undetected. You can fix weaknesses before they get exploited. After conducting a pen test and addressing its findings, you will have stronger defenses against intrusions and breaches, greater confidence that your data is safe, and less downtime.

When you need pen testing, RedTeam Security is ready to help. We have the expertise to thoroughly test your systems’ physical and technical security, uncover any problems, and let you better protect your data. To schedule a free consultation, call us at 612-234-7848.

Penetration testing isn’t a simple matter, though. It requires bringing in security professionals, planning a test period, and managing the tests. It takes time away from other work. A procedure that invites attacks, even by ethical hackers, makes IT people nervous. You have to consider when you can make the strongest case for a security assessment that includes pen testing. Sometimes testing is a necessity, and in many other cases, it provides strong benefits.

How Does Penetration Testing Aid Cybersecurity?

A penetration test is a set of authorized, controlled attacks on an information system to uncover weaknesses without doing harm. The testing team consists of specialists who know the types of attacks that most often succeed and tailor them to the target system. The client gets a detailed report on any weaknesses which the tests uncover.

Pen testing isn’t restricted to direct probing of the target system. It addresses real-world security issues of all kinds. It goes after human error through phishing emails and spoofed phone calls. It may also include tests of physical defenses, such as impersonating legitimate visitors and picking locks.

Pen testers use a “black box” or “white box” approach. Black box testing gives the pen testers no information beyond the target’s location. White box testing gives them some information about the network infrastructure.

Don’t confuse penetration testing with vulnerability scanning. A vulnerability scanner probes for known weaknesses, such as those listed in the Common Vulnerability Database, but it doesn’t try to exploit them. It’s a simpler technique that runs as an automated process. While it’s a valuable part of a complete information security toolkit, a vulnerability assessment isn’t a replacement for penetration testing. Some outfits claim to offer penetration tests when they merely scan for vulnerabilities.

What Are The Top Penetration Testing Scenarios?

The clearest case for pen testing comes when it’s a requirement. You could be obligated to use it because of regulations, industry standards, or contracts with vendors and customers. Even when it’s not an explicit requirement, it can be an important part of fulfilling a broad security mandate.

Regulatory Requirements

In the United States, the Federal Risk and Authorization Management Program (FedRAMP) requires penetration tests in certain cases. Systems seeking a Moderate or High authorization must conduct a penetration test, and they need to repeat it for each annual assessment. The guidelines call for comprehensive reporting. If you have to conduct such a test, you should cover all attack vectors identified by FedRAMP and include a phishing test.

HIPAA doesn’t require penetration testing for systems that fall under its jurisdiction, but you need to conduct a risk analysis that includes the evaluation of security controls. Running a pen test helps to satisfy this obligation. If your systems store protected health information (PHI), periodic penetration testing is highly recommended.

The GDPR requires “a process for regularly testing, assessing and evaluating the effectiveness of technical and organizational measures for ensuring the security of the processing.” The appropriate level of security depends on the risk level.It doesn’t specifically require penetration testing, but if your systems hold a large body of personal data on EU citizens, testing will go a long way toward demonstrating compliance.

Industry Requirements

When data security is critical, industry standards may mandate pen testing. The PCI council requires it for critical systems that process credit card data. Web applications that only pass confidential information without storing it generally aren’t obligated to conduct tests.

Banking and financial services operate under strict network security requirements almost everywhere. Penetration testing is sometimes a requirement or is listed as a way of complying. The Federal Deposit Insurance Corporation requires insured banks operating in the United States to maintain the security of their systems. It strongly encourages penetration testing as part of their security programs.

Systems that comply with the ISO 27001 standard have to prevent the exploitation of technical vulnerabilities. Penetration testing isn’t an explicit requirement, but it’s one of the best ways to demonstrate compliance.

Contractual Requirements

If you enter a contract that involves sensitive data, your vendor or customer may insist that you conduct a comprehensive risk assessment, including a penetration test. You will need to carry out the test, review the results, and remedy any serious problems found before going into operation. 

The testing could address interfaces to business partners’ systems as well as their data. Everyone needs to agree and understand what systems the penetration tester will probe and what is out of scope.

Audits and Reviews

Your business’s policies may require regular security testing and audits. Remediation after a security incident may call for a thorough test of network security. Penetration tests are an important part of the process. Monitoring and vulnerability scanning are valuable, but a network’s behavior when it’s under attack shows better than anything else whether its security works.

The term “audit” often means an evaluation of a business’s policies and processes, rather than its technical safeguards. A thorough audit, though, will include an examination of technical and physical protections.

When And How Often Should You Pen Test?

Running a penetration test isn’t just a one-time action if you want to maintain a high cybersecurity level. You should run tests when introducing a new, security-critical web application or service before going into full production. Waiting till you have a serious security incident is a poor strategy.

How often you should run tests depends on your cybersecurity requirements. Testing should happen at least once a year. If the cyberattack level is especially high or the consequences of penetration would be disastrous, quarterly testing is safer. If there is a major change in the network, such as moving to a different Web server or a new major release of the operating system, you should seriously consider including pen testing in the transition process.

Whenever possible, the tests should happen before going to full-scale production. The process is inherently disruptive, and it’s better to identify problems before the systems have full public exposure.

What Is The End Result Of A Penetration Test?

The principal deliverable of a pen test is a detailed report. It should include:

  • An executive summary    
  • Enumeration and discussion of the risks discovered    
  • The potential impact of the risks    
  • Recommendations

The first part will summarize the findings, evaluating the system’s security posture and highlighting the most important findings. A list of the specific problems will follow. The possible consequences of each risk can be included with its description or in a separate section. Finally, the report will recommend possible remedies. 

Most risks fall into a relatively small set of categories, including but not limited to the OWASP Top 10. Among them are:

  • SQL injection    
  • Cross-site scripting    
  • Access and authorization issues    
  • Misconfiguration of the application or Webserver    
  • Exposure of sensitive data

Many of these problems have well-known solutions and can easily be fixed once you identify them.

The recommendations may include multiple options. Some problems are easy to fix by changing the software’s configuration, installing updated software, or tightening the firewall settings. Others require serious work and take some time. Temporarily disabling some functionality may be the best quick fix, but the tester doesn’t necessarily know if that’s feasible. Alternative recommendations could include restricting access or adding a Web application firewall (WAF).

Get Testing And Boost Your Cybersecurity

Penetration testing will tell you how well your systems can stand up against intrusion attempts, malware, and phishing. You will emerge with greater confidence that your online defenses are up to the job, or else you’ll know what security vulnerabilities need fixing. Set up a free consultation with RedTeam Security cybersecurity experts to learn more about how pen testing can help you. Call 612-234-7848 today to get started.

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