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What are the five stages of penetration testing?

Pentesting is defined as the process of identifying the security vulnerabilities in a system or network and subsequently attempting to exploit them. The results these exploits play a critical role in finding and patching security flaws... including ones that may not be causing concern yet, but likely would in the future.

In this article, our team of ethical hackers discusses the responsibilities of a penetration tester and outlines the five penetration testing phases.

Let's get started:

Penetration Testing Stage #1: Reconnaissance 

The first stage, Reconnaissance, is the foundation of the entire process. In this phase, the tester embarks on an intelligence-gathering mission about the target system. The collection might encompass a variety of data, including information about IP addresses, domain details, network services, mail servers, and network topology. 

This proactive intelligence gathering provides invaluable insights, helping to sketch a detailed blueprint of the target's environment. Armed with this information, the tester can devise an informed testing strategy that can effectively probe for vulnerabilities, setting the stage for the subsequent phases of the penetration testing process.

Penetration Testing Stage #2: Scanning

Next comes the Scanning stage. This phase involves an in-depth technical review of the target system. Automated tools like vulnerability scanners, network mappers, and others are used to understand how the target system responds to various intrusions. 

Scanning enables testers to determine how the target application behaves under different conditions and to identify potential weak points that could be exploited. It maps out the system's digital terrain, enabling the tester to spot possible points of ingress that an attacker might use.

Penetration Testing Stage #3: Vulnerability Assessment

The process proceeds to the Vulnerability Assessment stage once the target system has been thoroughly scanned. This phase is a careful analysis of the target system to identify potential points of exploitation. 

Using a combination of automated tools and manual methodologies, the tester scrutinizes the security of the systems, identifying any potential loopholes. This meticulous assessment ensures a complete understanding of the system’s security posture, flagging potential vulnerabilities that cybercriminals could exploit. 

Penetration Testing Stage #4: Exploitation

Once the Vulnerability Assessment is complete, the next stage is Exploitation. In this critical phase, the tester attempts to capitalise on the vulnerabilities discovered. The aim isn't to cause damage but to ascertain the depth of the vulnerability and assess the potential damage it could cause. 

Exploitation might involve data breaches, service disruption, or unauthorized access to sensitive information. This stage needs to be carefully controlled and monitored, to ensure that the system isn't accidentally damaged during the process. It’s a delicate balancing act between pushing the boundaries and maintaining the integrity of the system.

Penetration Testing Stage #5: Reporting

Last but certainly not least comes Reporting, the final stage of any pentesting endeavor. During this, the tester or testing team compiles a comprehensive report detailing their findings. This includes the vulnerabilities discovered, data exploited, and the success of the simulated breach. 

However, the report is not just a list of issues. It also offers recommendations for addressing the vulnerabilities, including software patches, configuration changes, and improved security policies. The report serves as a roadmap, guiding the organization toward a more secure IT infrastructure. 

Reasons Why Your Organization Needs Periodic Pentesting

There are many benefits to performing penetration testing. Some of the key ones include:

• Maintaining compliance: Many organizations must undergo periodic penetration tests to comply with laws and regulations like the Payment Card Industry Data Security Standard (PCI DSS) and the Health Insurance Portability and Accountability Act

• Preventing cyberattacks before they occur: One of the main benefits of penetration testing is finding vulnerabilities in systems. These problems can then be addressed before hackers exploit them

• Avoiding costly security incidents: Penetration testing can help improve an organization’s security posture. Performing penetration tests helps organizations save money through making themselves less susceptible to attacks

Why Invest in Certified Ethical Hackers for Pentesting?

Shortening the average cyberattack is far from the only reason for organizations to invest in certified ethical hackers.

In 2023 alone, 40% of Canadian organizations have faced over 250 security-related threats, 73% claim that it takes over a week to recover from a cyberattack, and 62% say gaps in their in-house IT team's security skills reduce their ability to prevent cyber-related incidents. These statistics point to a rising trend where organizations of all sizes (and across all industries) are suffering avoidable financial losses as the result of preventable cyber breaches.

By investing in a quality team, you ensure that:

• Cyber insurance requirements are not just met but surpassed

• Threats are prevented before they occur, saving millions in financial and reputation-related damages

• Quick engagement starts with steady communication is guaranteed

• No outsourcing is being paid for: instead, highly specialized ethical hackers are providing the most thorough pentest for your organization

• There are no false positives found

Here at Packetlabs Ltd., we take cybersecurity beyond the checkbox. Packetlabs is a SOC 2 Type II accredited cybersecurity firm specializing in penetration testing services. To strengthen your security posture, we offer solutions such as penetration testing, adversary simulation, application security and other security assessments.

On top of employing only OSCP-minimum certified ethical hackers, the Packetlabs difference boils down to our 95% manual penetration testing. Instead of outsourcing our work or relying on automated VA scans, we guarantee zero false positives via our in-depth approach and passion for innovation: our security testing methodology is derived from the SANS Pentest Methodology, the MITRE ATT&CK framework for enterprises, and NIST SP800-115 to ensure compliance with the majority of common regulatory requirements. Our comprehensive methodology has been broken up based on which areas can be tested with automation and those which require extensive manual testing.

Alongside recently celebrating our twelfth year in business this year, our 95% manual penetration testing yielded a partnership with the SickKids Foundation, which was another one of our 2023 highlights: the SickKids Foundation is a fundraising organization based in Toronto that supports the Hospital with sick children. With over 1.5 million active donors, the foundation collects and manages sensitive information, which could result in reputational damage and loss of donors if breached.

The Different Types of Pentesting

Penetration testing is not one-size-fits-all.

At Packetlabs, our flexible offerings encapsulate:

• DevSecOps: DevSecOps is integrated early in your development cycle and acts as an extension of your development team to flag vulnerabilities within your existing detected management systems

• Red Teaming: Red Teaming is a full-scope simulated attack designed to get a holistic review of the level of risk and vulnerabilities across people, processes, and tech in an organization

• Purple Teaming: Purple Teaming is our collaborative testing exercise where the Packetlabs red team works with your internal security operations team (or blue team) to bridge the gap between offensive techniques and response efforts

• Cyber Maturity Assessments: A Cyber Maturity Assessment supports the tactical direction of your cybersecurity strategy. As the first step in strengthening your security posture, this assessment generates the roadmap to strengthen your overall security program

• Compromise Assessments: A Compromise Assessment uncovers past or present threats like zero-day malware, trojans, ransomware, and other anomalies that may go unnoticed in standard automated vulnerability scans

• OT Assessments: OT Cybersecurity Assessments simulate the likelihood of an attacker reaching the control centre from an external and internal perspective with production-safe testing

• Ransomware Penetration Testing: A ransomware penetration test evaluates the preparedness and risk of a ransomware attack and identifies gaps in people, processes, and technology, to determine the likelihood and readiness for a ransomware attack

• Cloud Penetration Testing: Multiple perspectives help with strengthening your security posture. These include Cloud Penetration Testing, which simulates an attacker in the environment, and a Cloud Penetration Review, which provides insights into cloud-specific vulnerabilities originating from an insecure configuration. Each of these services can be conducted separately or, for maximum effectiveness, combined as an enhanced cloud security bundle

• Objective-based Penetration Testing: Following a preliminary penetration test, objective-based testing conducts a more advanced simulated cybersecurity attack. The test is conducted by persistent ethical hackers who deploy multiphase attacks to gain access to your organization's data so that you can discover gaps and vulnerabilities unique to your organization and test your ability to detect and respond to threat actor

• Application Security Testing: More targeted in scope than a regular pentest, application security testing uncovers vulnerabilities residing in your web and mobile apps. Application Security Testing actively explores your application from an attacker’s perspective

• Infrastructure Penetration Testing: An infrastructure penetration testing assessment uncovers vulnerabilities in your IT and network systems and provides a tailored approach to each environment

These are in addition to the Packetlabs Portal, which enables you to quickly view findings, prioritize efforts, request retests after remediation, and monitor progress.

Conclusion

Successfully executing each of the five stages of penetration testing is crucial for generating actionable findings for you and your team.

If you're reading this, you are already in the market for a pentest. Contact our team today for your free, zero-obligation quote or download our Buyer's Guide below to take the next step.