What is Penetration Testing?

Ayush Parti
August 8, 2022

Penetration testing is a key component in any cyber security process. It enables companies to identify and fix weaknesses in their systems. These are weaknesses, which could be exploited by hackers or cybercriminals. But… what exactly is penetration testing?

Penetration testing (also known as pen-testing) is a simulated attack performed on a system or digital infrastructure to expose any vulnerabilities in operating systems, application software, or network devices.

In other words, pen testing is a form of ethical hacking. Think of it like trying to break into your own house so that you know where your weak points are. Once you have this information, you can improve your security in an effective manner. In future, if a real threat (like a robber) tries to break in they will be unsuccessful!

Penetration testing has never been more important than it is today. Sophisticated cybercriminals have countless weapons at their disposal: DDoS attacks, ransomware, cross-site scripting, and countless others. How can you ensure you are safe at all times?

Anonymous hacker

The best defense begins with knowing your vulnerabilities. If you fix them before any outside party can exploit them, it will give you peace of mind and save you money in the long run. Pen-testing provides valuable insights on how you could be attacked and what steps you need to take to secure your digital assets.

How Does Penetration Testing Work?

Penetration testing can be performed in two ways:

1) Manually, by cyber security professionals known as pen-testers.

or

2) With the help of technology, known as automated penetration testing.

We will discuss the key differences in both forms of pen-testing later, but the process is more or less the same:

A pen-tester will first perform an authorized attack to attempt to gain access to internal systems. These include servers, web applications, or other parts of a system.

If they succeed at breaching the system security, pen-testers will try to achieve the highest level of access that is possible.

Insights on security vulnerabilities will then be compiled and shared with IT managers and developer. Based on these reports and the level of security risk identified, they will take appropriate measures to fix gaps in their online security systems.

What Are The Different Stages of Penetration Testing?

Hacker

The entire penetration testing process broadly consists of five stages: 

  1. Reconnaissance (Planning)

As a first step, the pen-tester will aim to gather as much information on the system as possible. This is also known as “reconnaissance” or a preliminary survey.

Network topology, user accounts, and a system's defenses are examples of data collected. This helps a pen-tester plan an effective attack

strategy.

  1. Discovery

After gathering information, a pen-tester uses various tools at his disposal to identify potential entry points. He looks for weaknesses from which he can infiltrate the system. The goal of this stage is to find as many entry points and areas where an attack can be launched and document it. It is important to note here that this is different from a vulnerability assessment!

  1. Intrusion Attempt

This is where the real action begins! After the plan has been finalized, a pen-tester will attempt to infiltrate the system. He will also work on maintaining access to escalate privileges within the target environment. 

As mentioned earlier, this stage aims to intrude the system from every point of entry and as deeply as possible to find vulnerabilities. This is the most important part of the pen testing process.

  1. Clean up 

Once a system has been infiltrated and findings have been documented, a pen-tester will likely make sure they remove any evidence of a breach that a real attacker could leverage before the security gaps have been filled.

  1. Reporting and Retesting

Finally, a pen-tester will compile all findings and insights from the intrusion and generate a detailed report on every step of the process. This may also include advice or suggestions for remediation. This is the most valuable part of the process as it allows a client to gain information about which security weaknesses exist in their system and take action accordingly. 

You must conduct penetration tests regularly to ensure the highest level of security. It is crucial to re-test systems because new vulnerabilities will emerge over time.

How Much Access Do Penetration Testers Need?

You might be wondering what kind of information you would need to give a pen test firm or a penetration testing expert. For them to conduct an assessment of the target system, certain information may be needed. The answer is highly dependent on the type of vulnerabilities you are trying to protect your system against.

A woman on a laptop conducting a penetration testing assessment
You may need to grant a certain level of access for pen-testers to conduct an assessment.

For example, if you are worried about a hacker exploiting your system from the outside, the security measures needed would be different from a scenario where you suspect your system is already compromised. Once your system has been hacked, can the hacker gain access to critical and core data? What about security flaws that exist in your internal database? In order to assess all kinds of security risks, different levels of access may be granted to a penetration tester.

There are three separate levels of pen testing access:

Transparent Box

"Transparent box" pen testing is when pen testers have complete access to internal data. This includes source code, containers, and other essential information of a computer system.

This allows pen testers to create an effective strategy. Since they will have an idea of potential weak points beforehand, they can plan quickly. 

Semi-Opaque Box

A pen tester will have some information about your system and credentials while trying to uncover vulnerabilities.

 Usually, the amount of information is non-confidential information which an outside entity would be able to gather themselves. Sharing some information serves a valuable purpose as it saves time and thus allows targeted testing of security loopholes.

Opaque Box

In an "opaque box" system, the pen test professional does not have any prior knowledge of vulnerabilities or security issues. 

A pen tester must perform a blind test, much like a hacker would. This has many benefits as it emulates real-world attacks. It is also known as double-blind testing.

Optimal security might require more resources–but its usually worth the effort.

What is the Difference Between Manual Penetration Testing and Automated Penetration Testing?

You might be wondering what type of pen testing would be most optimal for your business. Well, the answer is: it depends. The key difference between automated vs manual penetration testing is in how it is conducted.

Here is a table for you to decide what may be a better option for you:

Why is Pen Testing Important?

Apart from safeguarding digital assets, there are a few major reasons why pen-testing is crucial for your business: 

Essential for Regulatory Compliance

Penetration testing helps companies get SOC 2 and ISO 27001 compliance. If you are  an organization which stores client information on the cloud you would need these regulatory approvals.

Many companies expect SOC 2 compliance. Having pen-testing reports along with patch reports can help verify that the required security measures are in place. Not only does this ease regulatory approval but also improves brand perception and gives you a competitive edge.

Helps you Divide Resources More Efficiently

A pen-test provides you with important information by letting you know which vulnerabilities need to be fixed immediately and which ones have a lower priority. This allows you to divide your team members’ time to fix security gaps optimally and use your company budget in a more efficient manner.

Establishes Trust and Credibility With Customers

By investing in pen-testing and taking adequate security measures, you are letting your customers know that you can be trusted when it comes to handling their data. This greatly improves your reputation and credibility.

Cost-Effective

What's the ROI of pen testing? Consider this: the average cost of a data breach in 2021 was reported to be $3.61 million according to a report by IBM.

An SOC 2 audit and pen-testing is a proactive method of ensuring safety and peace of mind. Data breaches are one of the most worrisome threats to any company.

What are the different types of Penetration Testing?

There are different subtypes of pen-testing services available as they vary in scope, cost and duration. Some of them are:

Web Application Testing

Penetration testing is often used to augment a web application firewall (WAF) in the context of web application security. As the name suggests, this type of cloud pen testing focuses specifically on testing web applications to detect vulnerabilities.

External/Internal Pen-Testing

External penetration tests are a subset of penetration testing where the “perimeter” security controls are assessed, i.e. the systems which are directly accessible from the internet. Conversely, an internal penetration test is a scenario where it is assumed an attacker already has breached your perimeter.

and has inside access to determine any potential internal threats. Ethical hackers then aim to formulate a plan to solidify network security from the inside and patch detected vulnerabilities.

Social Engineering

Social engineering primarily revolves around acts of deceiving people who work for an organization. Under this type of pen-testing, an ethical hacker would aim to exploit any vulnerabilities in employees. or people who would have access to sensitive digital assets.

For example, a pen-tester might try to impersonate a senior staff member to request sensitive data from an employee. He may also conduct a phishing scam to fool employees into handing over information.

Wireless Penetration Testing

Wireless pen-testing involves hacking into a wireless network to discover vulnerabilities. While this term might seem ubiquitous now, penetration testing has been around since the 1970s. During that era most computer systems were wired and required a different approach for assessing security gaps, therefore this distinction was necessary.

Mobile Application Testing

Mobile application pen-testing involves testing a mobile operating system/mobile applications for any security vulnerabilities. Mobile devices are frequently susceptible to a cyber attack in the modern world as businesses utilize such technology in their network infrastructure more than ever before.

What is Teaming in Pen Testing?

Teaming is an important term that pertains to how a pen test is being conducted. 

For a manual pen testing team, teaming acts as a simulation or “exercise.” These exercises are a way to research and understand how attacks may occur. There are two teams: The attacker and the defender. A more detailed explanation is given below:

Red Teams

The “red team” is the attacking team. The red team plays the role of the hacker. Their goal is to:

  1. Identify and assess vulnerabilities.
  2. Break the system’s defenses
  3. Test the security infrastructure.
  4. Viewing alternate options for attack.
  5. Reveal any limitations and security risks for that organization. 

Blue Teams

The blue team is the opposing or “defensive” team. Their goal is to prevent the red team from accomplishing their tasks. Some of their other goals include:

  1. Updating security systems.
  2. Taking proactive measures against potential attacks. 
  3. Fixing and remediating security gaps.
  4. Detecting false positives.

Purple Teams

Purple teams are a relatively new concept. Their function is a combination of both red and blue teams. The end goal is to comprehensively assess the cyber security of an organization. A better way to view a purple team is a dynamic between the red and blue teams.

When Should You Conduct a Penetration Test?

Penetration tests should ideally be conducted on a regular basis. However, there are a few specific scenarios where it is crucial to conduct a penetration test to ensure the safety of your digital assets:

1. Whenever there are any updates to your applications or digital infrastructure.

2. Whenever new applications have been built.

3. Whenever your company expands or establishes new locations.

4. Whenever patches have been applied to your software or infrastructure.

5. Whenever you have implemented new security features.

Heyhack: Automated Penetration Testing for SaaS Businesses

Heyhack is a web app security platform and penetration testing tool. It continuously scans your web app and APIs for unknown (zero-day) and known web vulnerabilities. It also provides detailed information on findings so you can fix issues in a matter of minutes. It is one of the most cost-effective tools on the market which allows you to scan for vulnerabilities other pen-testing tools can’t recognize.

Heyhack is used by security engineers as a penetration testing system and a development platform that allows creating security tools and exploits. The framework makes hacking simple for both attackers and defenders.

We hope you found this guide to be helpful. Heyhack provides automated web application security testing for SaaS businesses. If you’d like to know more about how we can help you, get in touch!

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