In this blog, let’s first review the Rules of Engagement, followed by the main stages of the penetration testing process. Let’s get started!
Rules of Engagement (RoE)
Before any testing begins, the organization and penetration testers agree on Rules of Engagement (RoE) document.
This document clearly defines
- the testing scope, including which systems, applications, and network segments will be assessed
- the timeframe for testing, acceptable testing methods,
- The escalation protocols, designated PICs, and communication procedures
- the process for reporting findings and addressing vulnerabilities
The RoE ensures the test remains ethical, legal, and safe—preventing unintended downtime or legal complications.
7 Simple Steps of the Penetration Testing Process
Penetration testing follows a systematic approach to ensure that security assessments are thorough, accurate, and aligned with real-world threat scenarios.
Step 1: Planning and Reconnaissance
The process starts with a scope definition, goals, and legal limits. Testers gather preliminary intelligence such as IP addresses, domain names, and public employee data. This phase includes researching potential threat vectors relevant to the organization’s environment—ensuring the test reflects actual risks.
Step 2: Scanning and Enumeration
Automatic scanning tools are employed to find open ports, active services, and system information. Testers detect operating systems, software versions, and settings that expose vulnerabilities. Enumeration goes a step further into services exposed, which assists in mapping the possible entry points for attackers to leverage. This enables the identification of specific vulnerabilities for attack.
Step 3: Gaining Access
Testers try to take advantage of the vulnerabilities discovered using real attack methods such as SQL injections, buffer overflows, or credential brute forcing. The goal is to simulate unauthorized access and test the strength of existing defenses—closely mimicking real-world threat behavior.
Step 4: Maintaining Access
When entering, the testers mimic persistence, just like an actual hacker. They install rootkits, create stealth user accounts, or create backdoors to leave access open. This determines how long a threat actor can stay concealed and what kind of damage they can cause. It also tests the effectiveness of monitoring and alert systems.
Step 5: Analysis and Reporting
Once it is tested, a thorough report is developed. The report contains vulnerabilities identified, how they were exploited, and the access level attained. All issues are risk-scored, and remedial action is given. This last report features technical reports, together with executive summaries, designed to recommend improvements in security around the company.
Step 6: Remediation
This step focuses on resolving identified vulnerabilities through patches, configuration changes, or code fixes. Based on root cause analysis, security controls are strengthened to prevent recurrence. Organizations should also update policies and training if needed. Remediation tasks must be prioritized according to the severity of risks and their potential impact on business operations.
Step 7: Re-Testing / Verification
Once fixes are in place, a re-test is performed to confirm that all critical issues have been resolved and no new risks were introduced. This step also ensures that no new issues are introduced during fixes. A thorough validation process helps confirm the environment’s security posture and ensures all risks are mitigated before issuing a final sign-off or closing the assessment.
Preparation of Penetration Testing
Organizations must perform certain preparatory steps before conducting a pen test to make the process efficient and seamless.
Define the Scope
Prior to starting a penetration test, define clearly what systems and assets are to be tested. These could include web applications, internal networks, cloud resources, or mobile platforms. Defining the scope correctly ensures the test is focused, does not interfere with critical systems, and is aligned with organizational priorities and security objectives.
Set Objectives
Set the main aim of the penetration test to dictate its conduct. Are you ensuring compliance, staff training, incident response capability, or overall network resilience? Specific objectives render the findings actionable, relevant, and aligned with your organization’s risk management and cybersecurity improvement programs.
Notify Stakeholders
Before conducting a penetration test, effective communication should be done. Notifying all stakeholders involved, such as IT, legal, compliance, and executives, is essential. This would help avoid confusion, prevent alarm without action, and provide support throughout the testing period. The participants should understand the purpose, scope, and duration of the test.
Backup Systems
You need to protect data before any security testing. Take full system and data backups to ensure data integrity in case of accidental disturbance. Back up all the important systems, applications, and configurations and make them safe and recoverable. Test the backups beforehand to ensure that they work as expected.
Define Rules of Engagement
Develop a formal contract defining the scope of the penetration test. Define what systems or data are off-limits, what testing methods are acceptable, and what legal permissions are required. Establish emergency contact procedures. These procedures help maintain ethical boundaries and safeguard the testing staff and the organization legally.
Note: Preparation is required to achieve a safety and realism balance.
Post-Test Procedures
Once the test is finished, your team will then work on consuming the results and making enhancements.
1. Read the Final Report Thoroughly
- Search for high-severity and low-severity vulnerabilities.
- Understand each vulnerability’s business impact.
2. Remediate Based on Priority
- Fix high-risk vulnerabilities first.
- Schedule patching or configuration modifications for medium/low risks.
3. Apply Recommendations
- Apply firewall rules, IAM policy, or software patches.
- Enhance security awareness training if necessary.
4. Conduct a Follow-Up Test
- Ensure vulnerabilities are fixed correctly.
- Ensure that new issues do not arise during remediation.
- Test regularly to maintain your security as your systems increase.
Cover Up:
Penetration testing is a powerful tool for uncovering hidden security gaps before attackers do. When properly scoped and executed, it uncovers hidden vulnerabilities, validates the effectiveness of existing controls, and supports continuous improvement of your security posture.
The foundation of a successful test lies in establishing clear Rules of Engagement and preparing your teams with defined objectives, strong communication, and backup protocols. But testing alone is not enough—true value comes from applying the insights gained, remediating vulnerabilities, and re-testing to confirm resilience.
By partnering with a trusted cybersecurity provider like Digitraly, organizations gain access to skilled professionals who can simulate sophisticated threats, deliver actionable insights, and help build lasting cyber resilience in the face of evolving risks.
