If you’re responsible for the security of your company’s information systems and sensitive data, then you know that penetration testing is a critical part of maintaining that security. But do you know what goes into a successful penetration test? Typically there are five phases and in this article, we’ll discuss each phase in detail and provide tips on how to successfully perform them.

What Is Software Penetration Testing?

Software penetration testing is a security assessment methodology used to identify vulnerabilities in a software by simulating attacks on it. The goal of a penetration test is to exploit any vulnerabilities that are identified in order to gain access to the system or network, potentially leading to a breach of sensitive data.

How Can You Benefit from Penetration Testing?

  • It can help meet compliance requirements.
  • improves overall security posture
  • detects if any data breach is underway
  • prevents future breaches from taking place
  • helps to stay competitive and with public image
  • reduces system downtimes by patching buggy software and applications

The Five Phases of Software Penetration Testing

Phase One: Pre-engagement reconnaissance

During this phase, you’ll be gathering any information about the target software that you can find. The tester will compile a list of IP addresses, domain names, and other identifying information that can be used in later phases. They will also research the company’s online presence, looking for any publicly available information that could be used to gain a foothold into the company’s systems. In some cases, they may even contact the company to request information such as their security policy or contact info for employees who would have access to sensitive data. All of this information will help the tester in later phases when they are trying to identify vulnerabilities.

Phase Two: Vulnerability scanning

In this phase, the tester uses automated tools and manual techniques to scan for known vulnerabilities on the target systems. This includes looking for outdated software, open ports, and weak passwords. By identifying these vulnerabilities early on, the tester can focus their efforts on exploiting them later in the process.

Phase Three: Exploitation

This is where the real fun begins! In this phase, the tester starts actively exploiting any of the vulnerabilities that were identified in earlier phases. They may use exploits that have been publicly released or ones that they have developed themselves. By doing this, they can gain a foothold into the target systems and start extracting data.

Phase Four: Post-exploitation

Once the tester has achieved their goals and gained access to the target systems, they move into this phase. Here, they will take whatever data they have gathered and exfiltrate it out of the system. They may also stay in the system to gather more information or set up backdoors for future access.

Phase Five: Reporting and remediation

Finally, once all of the data has been collected and the testing is complete, the tester produces a report documenting their findings. This report is then given to the organisation’s security team who can use it to identify and fix any vulnerabilities that were found during the test.

Is Each Phase Compulsory?

No, all the phases are not compulsory and some can be skipped based on what you already know about that target system and what is required from the test.

However, it is important to remember that every phase is necessary for a successful penetration test and should not be skipped.

Penetration Testing Checklist

Penetration testing can be a very time-consuming process. To provide some structure, below is a checklist of what you can include in each phase.

For reconnaissance:

  • Compile a list of IP addresses, URLs, and other identifying information.
  • Research the company’s online presence.
  • Use OSINT tools to gather everything that is publicly available

For vulnerability scanning:

  • Use automated tools and manual techniques to scan for known vulnerabilities.
  • Identify outdated software, open ports, and weak passwords.
  • Check for known vulnerabilities online

For exploitation:

  • Identify and exploit any vulnerabilities that were identified in earlier phases.
  • Use exploits that have been publicly released or ones that you have developed yourself.

For post-exploitation:

  • Extract data from the target systems and exfiltrate it out of the system.
  • Stay in the system to gather more information or set up backdoors for future access.
  • Change security settings and/or account passwords

For reporting:

  • Create a detailed report on all the findings during the test.
  • Include remediation tips for each vulnerability as well as their threat level
  • Provide a recommended strategy to patch things up

In no way is this a conclusive list so get creative and think outside the box when testing.

How Often Should You Perform Pen Tests?

Ideally, you should perform pen tests every year. This ensures that your systems are always secure and up to date. If there is a vulnerability found in one of the tests, then it can be fixed before an attacker finds it themselves. In some cases though, performing these tests yearly may not be enough depending on how often changes are implemented. If that’s the case, you’ll need to hold it more frequently.


Penetration testing is an essential part of any security program. It helps ensure that your systems are secure and up to date, as well as identify any vulnerabilities before they become a problem.

To get the most out of your tests, you should be sure to include all five phases: reconnaissance, vulnerability scanning, exploitation, post-exploitation, and reporting.

Performing pen tests once a year is the ideal frequency, but it may not be enough in some cases. Be sure to adjust your schedule accordingly.