The Ultimate Guide to Penetration Testing: Everything You Need to Know

Penetration testing emulates real-world cyber attacks against your organization in a safe, simulated environment. It lets you better protect IT assets by uncovering the most vulnerable parts of your network and gaps in security.

What is Penetration Testing?

Penetration testing is an assessment delivered by an ethical hacking service to “penetrate” your network or a specific system. Pen testers simulate real-world cyber attacks using tactics and tools adopted by today’s threat actors. Why? To find insights that boost your security program before an actual attack occurs.

One of these vital insights is system vulnerabilities. By doing cyber attack “mock trials,” you can see where you’re susceptible. For example, areas of the network that are most exploitable or security control weaknesses that need improvements.

Types of Penetration Testing

Cyber attacks can target your business from all directions using various tactics. Hence, you can deploy many types of pen test services for complete security analysis:

• (External) network testing: Finds vulnerabilities in your internet-facing assets like firewalls, servers, and routers. It lets you find exploits hackers could target from the outside.
• (Internal) network testing: Identifies attack paths and vulnerabilities within the network. For example, misconfigured admin controls could let employees access unauthorized, privileged information.
• Web application testing: Evaluates your web app configurations, integrations, and controls. It helps ensure app security and that a hacker can’t get unauthorized access through the host site.
• Wireless assessments: Tests wireless security settings for on-premise networks. It checks if hackers could establish connections to your internal environment.
• Mobile app testing: Simulates attacks on iPhone and Android applications. You use it to find vulnerabilities in the app’s encryption protocols, configurations, and access controls.
• Social engineering & spear phishing testing: Tests user awareness through email phishing campaigns. It targets a list of employees or individuals to see if they’ll comply with a spoofed email’s request.
• Configuration review: Assesses on-premise or cloud environments. It looks at the servers, network, access controls, and security settings to find vulnerabilities a hacker could exploit.

Importance of Penetration Testing

93% of company networks are susceptible to a breach by a cybercriminal. Unfortunately, without regular pen testing, these organizations don’t know where an actual attack will come from or how.

Penetration testing lets you protect against cyber threats by pinpointing your weaknesses. Taking insights gathered from your pen test, you can:

• Fill in known security gaps with new controls
• Prioritize remediation efforts based on where you’re most vulnerable
• Find security flaws to make adjustments or add failsafe controls
• Remediate any system misconfigurations

Pen testing is proactive by nature. It lets you improve security before falling victim to an attack.

Penetration Testing Process

For the best results, pen-testing engagements emulate real-world attack scenarios. They often follow a structured process, with certain steps typically used by a cybercriminal:

• Planning: You and the pen testers create a plan of action, set goals, and establish the rules of engagement. Doing so ensures a smoother testing campaign that meets your security objectives.
• Reconnaissance: Pen testers get intelligence on your users, network, or target system. This data helps them pinpoint weaknesses they can exploit to gain access.
• Scanning: Pen testers use vulnerability scanning or network mapping tools to get visibility on the target system. They typically look for any points of entry they can use to carry out an attack later on.
• Exploitation: Pen testers try to access the target system using vulnerabilities found during the prior stages. The purpose is to confirm these vulnerabilities, attack and penetrate the system, and then escalate privileges for more elevated data access.
• Reporting: Pen testers share insights gathered during the testing process. This information gives recommendations and a roadmap to improve your security posture based on your most significant vulnerabilities.

Best Practices in Penetration Testing

While vital for security, penetration testing is often a costly process that is invasive on your IT stack. To maximize your experience and get the best possible insights, follow these useful tips:

Clearly Define Your Objectives

Before the engagement. Ask yourself, “What do we want to get out of this?” Is it for vulnerability management? To test current security controls? Check a box for compliance requirements? Or perhaps all of the above?

Ensure Proper Documentation

Maintain accurate records of your cybersecurity program and pen test results. This information keeps you in compliance with many guidelines and regulatory requirements. It also gives you a performance baseline to build on for future assessments.

Work Exclusively with Certified Professionals

Pen testing is a complex, rigorous process. You’re literally authorizing someone to hack your critical data systems, so don’t take shortcuts when engaging with providers. Look for robust experience in pen testing and team certifications such as Certified Ethical Hacker (CEH), Offensive Security Certified Professional (OSCP), or Certified Penetration Testing Engineer (CPTE).

Prioritize the Most Critical Vulnerabilities

With budgetary restrictions and only so much time in a day, it’s simply not practical to address every security flaw identified in the test results. Start with the most exploitable and the ones that could severely impact your business.

Challenges and Limitations

Bear in mind that penetration testing isn’t always foolproof. False positives, for example, show a vulnerability that doesn’t actually exist in the network. Alternatively, testing tools may generate false negatives — a vulnerability that does exist but wasn’t detected.

Much of the false flags occur because of pen test limitations. Regarding scope, you’re typically simulating attacks on specific areas of the network. If you, for example, only do social engineering & spear phishing tests, you’ll miss critical vulnerabilities in other areas, such as the network’s perimeter or within a web application.

You’re also limited in time. Pen testing generally only takes place over a few days or weeks. What about the vulnerabilities that pop up after that time frame?

Regulatory Compliance

Depending on your industry or the types of data managed, penetration testing lets you comply with various regulatory security requirements like:

• Payment Card Industry Data Security Standard (PCI DSS): For credit card information
• General Data Protection Regulation (GDPR): For personal data of European Union citizens
• California Consumer Privacy Act (CCPA): For the private data of California residents
• Health Insurance Portability and Accountability Act (HIPAA): For medical records and personal health information (PHI)
• North American Electric Reliability Corporation Critical Infrastructure Protection (NERC CIP): For securing the North American electric grid
• Cybersecurity Maturity Model Certification (CMMC): For contractors to protect sensitive government defense information

Pen testing is also required to get the “stamp of approval” for professional certifications like ISO 27001.

Penetration Testing: The Crucial Step Toward Enterprise Security Success

Penetration testing lets you answer the key question, “How would we withstand a real-world cyber-attack?” Through attack simulations by a professional, you can pinpoint your network weaknesses while evaluating security control effectiveness.