Penetration Testing 101 For Beginners

Penetration Testing 101 For Beginners

Penetration Testing

Presently, cybercrimes are as rampant as ever. In 2019, a study predicted that a ransomware attack hits businesses every 14 seconds. Today, it might be more frequent. What’s more alarming is that, according to IBM, it takes 200+ days for companies to detect and contain a cyberattack. The damage caused during these days is enough to take a massive toll on the status of a company.

Most of the time, business owners are too late to identify a security breach. After that, it is difficult to stop the attack and control the damage it can cause. Around 60% of small businesses fail within six months after a cyberattack.

The best thing you can do for your organization is to take up preventative measures against such attacks. One of the ways you can do it is by performing penetration tests regularly. If you’re not sure of what penetration testing is and how it works, don’t worry we’ve got you covered. This post breaks down everything you have got to know about penetration testing. So let’s dive right in!

What Is Penetration Testing?

Penetration testing is a popular security practice. It is also called pentesting or ethical hacking. It involves hacking into a system or application to study the vulnerabilities, how they can be exploited, and the damage they can cause if they’re exploited. 

Some people think that vulnerability assessment and penetration testing are the same. However, this is simply not true. Vulnerability assessment merely lists out the vulnerabilities in the system. On the other hand, pentesting will identify the magnitude of potential damage each vulnerability can cause. Vulnerability assessment can be viewed as the first step of a pentest. It is usually automated as opposed to penetration tests which are done manually.

Why Is Penetration Testing Important?

Penetration testing has been around since the 1960s and is still one of the best security practices.  There are numerous benefits of conducting a pentest.

  • You can prevent a potential security breach.
  • A penetration test can uncover and rectify any flaws or loopholes in security.
  • Conducting penetration tests can enhance data protection.
  • It can test the effectiveness of the existing web application firewall and other security defences.
  • Penetration tests also support GDPR compliance, as well as  ISO 27001, PCI-DSS, and HIPAA.
  • Conducting penetration tests increases customer satisfaction and trust.

Penetration Testing: The Process

5 Phases Of Penetration Testing

To ensure you’re getting the most out of a penetration test, you need to make sure it covers all the phases of penetration testing.

1. Defining Scope and Planning

One of the first things to do while conducting a pentest is to define scope. The tester is expected to gather some basic information regarding the company and the application. By doing so, they have to set some goals and expectations for the test.

Planning calls for acquiring all the data about the company that one can find easily on an open-source platform. This step is crucial because hackers can use this information against you. This is also called Open Source Intelligence (OSINT). Some of the popular OSINT tools available are Shodan and SpiderFoot.

  • Nmap: Nmap or Network Mapper is an extremely popular free and open-source recon tool. Linux Journal has given it the title “The Security Product of the Year”. It is typically used for network discovery and security audits. NMap can also be useful for managing service upgrade schedules, network inventory, and monitoring host or service uptime. It is easy, powerful, flexible, and portable.
  • Paessler PRTG: Paessler PRTG is another recon tool that you can use to monitor all the systems in your infrastructure IT. It is an easy and powerful tool created for all types of business, small or large.

2. Scanning

In this phase of penetration testing, the tester is expected to identify all the vulnerabilities present in the application. Then they are classified into external vulnerabilities and internal vulnerabilities. Also, testers perform two types of analysis while scanning for vulnerabilities. The first one is a static analysis where the tester scans the application in a single pass by assuming how it will behave during run time. The second analysis technique is a dynamic analysis where the tester scans the application in runtime.

Some tools that can help you with the scanning process include:

  • Nikto: Nikto is a scanner capable of executing extensive tests against web servers. This free, easy and fast scanner identifies 6500+ potentially dangerous programs, searches for outdated versions of 1000+ servers, and identifies version-specific problems on 250+ servers. 
  • OpenVAS: OpenVAS or Open Vulnerability Assessment Scanner performs a complete vulnerability check of an IT infrastructure. Some of its features are:
  1. authenticated or unauthenticated testing
  2. a range of internet and industrial protocols
  3. performance tuning for large-scale scans
  4. powerful internal programming language

3. Exploitation

During this phase, the tester exploits all the vulnerabilities uncovered in the previous phase. For doing so, they use various exploitation techniques like web application attacks such as CSS, SQLi, backdoors. Other exploitation techniques include network attacks and social engineering. One of the most popular tools that test defenses use is Metasploit.

  • Metasploit: Metasploit Framework is a Ruby-based platform that can help you exploit any security vulnerabilities you find using various exploits. It is also a recon tool. That is, it can uncover vulnerabilities and thereby make a great asset to a penetration test.
  • sqlmap: sqlmap is an open-source tool you can use to identify SQL injections. It can exploit 6 types of SQL injection attacks. Therefore, it is a great asset to a website penetration test. You can install sqlmap by cloning Git repository: git clone –depth 1 sqlmap-dev

4. Maintaining Access

After gaining access, it is equally important to assess the damage each attack will have on the application. The tester finds out what information is accessible to a hacker after compromising security and gaining access. They also identify how long a security threat can persist on your website without being detected. The objective behind this step is also to mimic advanced persistent threats on your website. These threats stick around for a long time and steal valuable information.

5. Analysis and Retesting

The observations and inferences of the test have to be compiled into a report. This detailed report should contain the vulnerabilities and how you can resolve them. After making the required changes, it is vital to conduct another penetration test. This will help you reassess your cyber security situation and observe the effectiveness of the fixes.

Pentest Checklist

1. Data Validation

  • Perform input validation
  • Use commit or rollback semantic for exception handling
  • Avoid or remove backdoors and shell escapes
  • Make sure you’ve validated the configuration files before use

2. Data Handling

  • Sensitive data must not be in code
  • Encrypt cookies that could contain sensitive information
  • Resource connection strings must be encrypted

3. Error Handling

  • Never display errors to users that would reveal sensitive information about the system/application
  • Make sure to include a safe mode for your application, which it can return to if any unexpected error occurs

4. User Management

  • Username enumeration
  • Resilience to password guessing
  • Test Oauth login functionality
  • Check for concurrent login through different machine/IP


Pentesting is a popular security exercise. It helps you uncover all the loopholes and weaknesses in your application and therefore, helps you secure it better. Conducting regular penetration tests will help you in numerous ways. Data protection, better security, and increased customer satisfaction to name a few.

A rigorous and effective penetration test can take anywhere between 2-3 days or 2+ weeks to complete, depending on the size of your business. And as mentioned before, it requires hundreds of scans and a variety of tools. So opting for a penetration testing service provider makes very much sense.

The Penetration Testing service provider of experts should identify all the vulnerabilities in your application and propose the best fixes for them. They should guide you through the whole testing process and assist 24/7.

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