How to Do Penetration Testing Step by Step

Technology evolves for both the good and bad. Tech gurus create new software and systems to make processes more accessible, efficient, and precise; while on the other hand, hackers evolve their techniques to exploit IT infrastructure weaknesses. 

That’s why companies invest in penetration testing activities—to spot and fix vulnerabilities before threat actors exploit them.

This blog will help you learn how to do penetration testing step by step, but first, let’s see what penetration testing is.

What is Penetration Testing?

Penetration testing, or pentesting for short, is a simulated cyberattack technique where an expert identifies vulnerabilities in an IT structure to fix them before someone uses them to their advantage. 

They mimic an attack by following all the possible paths through which hackers can infiltrate a system. Pentesting also assesses the ability of bad actors to breach a system unseen as many cyberattacks occur without an organization’s knowledge. 

Like anything, there are several risks and benefits of penetration testing. Still, in today’s cyber landscape, the pros typically outweigh the cons.

You can imagine pentesting as a situation where a millionaire secures all the points a burglar can use to enter their mansion. They’ll check all the windows, doors, basements, AC ducts, chimneys, roofs, etc. to ensure nobody can break into their building.

Now, let’s go through the steps required to perform penetration testing.

Step 1: Planning

Planning is the first step and a vital process in pentesting.

To secure your IT infrastructure from potential attacks,  you need to plan everything in advance. Here’s what’s outlined before starting the actual test.

What Are You Testing?

The process starts by understanding what information assets are present in an IT structure and how to classify them. Determining factors include the business functions they support, asset owners, and the sensitivity and criticality of each asset to the organization. 

An information asset is defined as any asset used to store, handle, or process data typically required to perform critical business functions (CBFs). These include servers, storage media, databases, computers, user devices, email communications, and paperwork records.

That’s why in-depth quantitative and/or qualitative analyses of each IT asset is also crucial for accurate classification.

Ultimately, asset classification helps determine what, when, and how often to perform penetration testing based on the following factors:

• The value of an IT asset to various types of cybercriminals.
• The sensitivity and classification of data stored, processed, and passing through the target system.
• The risk level and difficulty associated with the penetration test.

The first two factors determine the risks associated with the probability of a cyberattack and its repercussions (including costs) on business performance.

The higher the risk, the more important it is to pen – test the asset in question. This is similar to the millionaire assessing what a burglar can steal and how that would impact their net worth and reputation. 

The third factor helps determine the right time to perform the different stages of penetration testing to avoid interrupting business processes. Assess whether you’ve got the right workforce to conduct the test or if a third party is required. 

Although hiring a third-party expert increases the overall cost, it’s still recommended for high-value asset pentesting.

Define the Test Elements and Scope

IT systems are interlinked, so they often interact with other external and internal frameworks and applications. Also consider the physical, technical, and administrative controls. They’re vital to understanding how to do penetration testing for the target system. 

Pentesters must define the number of attack paths to the system and identify the test elements. This helps them plan which penetration testing tools and skills are required.

Define the Best Outcome

The pentester must understand the organization’s expectations from conducting the test. They can seek this by getting answers to these three questions:

1. What are the current operational procedures, and how is the company shielding them?
2. What are the differences between the protection of current operational procedures and what the organization expects?
3. Which security vulnerabilities need to be tested and patched?

You can understand this as what expectations the millionaire would have from the security team they hired to make their house theft-proof. The team evaluates the current security systems to identify any problems, changes, and improvements to meet the expectations of the millionaire.

What Are You NOT Testing?

Although hackers often disrupt critical business operations, most organizations won’t permit that for network pen tests.. For example, exploiting software meant for sales can shut down the entire system, impacting the business until the vulnerability is patched.

That’s why the organization must clearly define what is permitted and what isn’t during the test. Other test boundaries include what data can be accessed and whether attempted password cracking is allowed.

If we relate this with the millionaire example, then this situation is where they’ll create specific boundaries for the security team because it would be potentially risky to allow access to bank accounts, safes, or other expensive possessions.

Get the Project Approved

Lastly, irrespective of the penetration testing type, an expert must get approval before starting. They should have clear test boundaries, permissions, test elements to be affected, etc.

Step 2: Attack Simulation

The ultimate penetration testing goals are to secure essential data from malicious actors and different types of cyberattacks. An ethical hacker performs the simulation in multiple steps that start by collecting passive data and end by analyzing the gaps. 

After the planning phase, here’s how to do penetration testing step by step:

#1: Get Passive Data

The first step involves collecting passive information about the target system and company to understand how it works during day-to-day processes. 

This process is coined under various terms like discovery, reconnaissance, scanning, or probing but describes the same thing:. assessing the complete operating environment, potential vulnerabilities, and available attack vectors of the target system. Public information can be a valuable resource for cyberattackers, so pentesters must also use such data to their advantage.

#2: Start the Active Testing Stage

In this stage, an ethical hacker tests the various attack paths within the boundaries set by management. It includes both static and dynamic analysis. 

In static analysis, internal components of the target IT structure are tested and the attack paths are modeled before evaluating the vulnerabilities. It includes examining application binaries, source code, and byte code for any exploitable weaknesses.

Conversely, dynamic analysis involves penetration testing activities performed while a program is in operation. It includes examining and attacking a system in its running state to find any security vulnerabilities. 

Deploying malware via email, brute force attacks, Denial-of-Service (DoS) attacks, control bypass attempts, and any other active penetration tactics may fall under this step. 

Once the pentester gains access to the target system, all other identified attack pathways and assets must be scanned, mapped, identified, and tested. 

#3: Analyze the Data

Next, the testing team evaluates the collected test result data to understand attack paths and how threat actors can compromise system components within the target structure.

#4: Assess Access Outcomes

Here, outcomes of any interactions between the target structure and the other operating system elements identified in the previous steps are analyzed. This step also assesses the types of connections, how they’re secured, and any exchanged data.

#5: Correlate the Gathered Information

Pentesters must then reconcile the collected information. This data, correlated with all the previous steps, help get a clear picture of the system, its operating environment, and its vulnerable aspects. 

#6: Create Safe Operation KPIs

Next, the ethical hacking team determines how optimum protection can be achieved based on the analyzed data. They create metrics to measure current and future states at which the system can safely operate. This state is either created or reviewed.

#7: Perform Gap Analysis

The last step in attack simulation is gap analysis. Here, pentesters must assess how the system should operate and be protected versus its current state to identify security gaps.

Step 3: Reporting and Risk Analysis

The gap analysis report is created by assessing any successful cloned attacks. The testing typically compiles two separate reports. The first one is for management; it’s not as technically detailed and contains meaningful, business-related information on the potential impacts of the identified vulnerabilities.

The second penetration testing report is for the IT team. It includes detailed information on pentesting outcomes to help assess risks and identify solutions to patch security weaknesses. 

The report should also contain key metrics to help the organization conduct risk analysis, classify the severity of each identified risk, and identify the best solutions for the most significant risk reduction.

Step 4: Retesting

Once the report is submitted, remediation recommendations are followed by the company’s IT team to patch the identified security weaknesses. Retesting is then conducted after 2-3 months to check whether the vulnerabilities have been effectively remediated.

Summary

Performing penetration testing is a vital part of cyber protection. It helps identify vulnerabilities hackers can exploit to breach your systems, gain unauthorized control, access confidential data, and ultimately harm your organization.  

Pentesting starts with in-depth planning like understanding what has to be tested, the elements and risks involved, and the boundaries set by the management team.

The actual test begins by collecting and analyzing passive data to actively simulating an attack and then correlating the gathered information. This helps in setting metrics to measure current and future states for optimum protection. 

Once the test is conducted, it’s crucial to analyze the security risks and identify optimal solutions. Your IT team should follow the remedial recommendations to ensure your systems are attack-proof.