7 Steps to Comprehensive Penetration Testing

What’s a Comprehensive Penetration Testing Approach?

The term ‘security assessment’ is used to describe the process of assessing a system, such as a network or an application, to find security flaws that can lead to cyber-attacks. There are several ways to perform security assessments for a system. At Software Secured, we follow a comprehensive penetration testing approach, combining the latest hacking techniques, which are manually executed by our experienced engineers. In addition, we apply our proprietary testing stack, advanced threat modelling, and real-time portal dashboard for reporting, giving you the best coverage and depth in the industry.

Conducting Vulnerability Assessment in Penetration Testing: Techniques and Tools

Vulnerability assessment involves analyzing threat sources and identifying targets to map potential attack vectors. Penetration testers use various techniques to probe the target network, uncovering vulnerabilities such as open authentication access, directory structures, and remote-code execution possibilities. The process often includes DNS interrogation, InterNIC queries, and network sniffing to gather hostnames and IP information. Automated and manual vulnerability scans are conducted to test systems against known vulnerabilities and discover new ones. Testers may utilize resources like the National Vulnerability Database and tools such as Tenable, Rapid7, and Nmap. They also assess high-value assets, including employee and customer data, technical information, and internal and external threats. Web application attacks, such as cross-site scripting and SQL injection, are employed to exploit vulnerabilities and escalate privileges.

Three Factors We Focus on Optimizing

1. Coverage

We use several techniques in our approach to automate the discovery of basic attacks. We continue pushing the boundaries of what tools are capable of finding, giving us the chance to spend more manual testing time on finding harder-to-discover vulnerabilities, such as business logic vulnerabilities. Quarterly deep assessments to locate vulnerabilities and continuous re-testing on patched issues ensure that the application is covered year-round, both during and between major releases.

2. Depth

We follow a stringent process, combined with a checklist of over 200 security items that are reviewed in every assessment. Our checklist is continuously updated with the most recent techniques to ensure that as many code paths in the application have been tested. Better yet, our pentesters apply their creativity and intuition to go deeper, finding new vulnerabilities beyond the checklist, and creating a truly comprehensive test.

3. Comprehensive testing

We spend a fair amount of time understanding the business purpose of the application through threat modelling, allowing us to go deeper and understand the attacker’s motivation. By assessing various use cases, we unlock insights into potential vulnerabilities in the application design that would otherwise remain hidden.

Our Seven-Step Assessment Process

Given our three areas of focus, we follow a seven-step process with every assessment:

1. Reconnaissance

This stage is all about understanding the application and its unique business logic. Meetings with the client and pen test provider help ensure that all parties are well-informed about the test. The test environment must be ready at this point.

2. Threat Modeling & Custom Security Test Plan

Building out a threat model is essential to understand the common use cases of the application. An effective threat model can also identify security risks in the design of the application, which may be difficult to change at a later stage. However, understanding these risks early helps prepare the rest of the security plan to work around them.

3. Development of Custom Scripts to Assist with Testing

The fun begins. Pen testers start diving deep into the application with a mix of manual and automated approaches.

4. Identification of Zero-Day Vulnerabilities

As critical vulnerabilities are identified, the client is notified immediately. Steps to reproduce the issue are shared with the client so that their development team can begin remediation as soon as possible.

5. Exploitation & Escalation

The less severe vulnerabilities found during the early stages of the pen test are exploited and escalated as much as possible without affecting the function of the application (for instance, if a pen tester is testing a vulnerability and it risks taking down the entire application, they’ll take it as far as possible without creating any actual harm). Test environments and test accounts are created to prevent any real damage and exploitation of the live application.

6. Cleanup & Reporting

Upon completion, pen testers will gather all found issues, regardless of severity, into a report. A good penetration testing provider should also include steps for replicating the issue so that the client’s development team can mitigate the issue.

7. Retesting & Certification

After the report is delivered, the client may patch several vulnerabilities. A quality pen test provider will be able to retest these known vulnerabilities shortly after to verify that they have been fixed correctly or sufficiently. In some cases, the pen tester may require that the client develops a complete fix, and in other cases, a “band-aid” solution may suffice for critical issues that need deeper attention later.

When all is good to go, the pen test provider can offer a certificate to the client as proof of application security. This certification is essential when earning compliance, such as SOC 2 or ISO 27500. It’s also helpful for closing enterprise deals (learn more about vendor security questionnaires here) or for startups that want to generate higher investor appeal.

Penetration testing methods

Not every pentest engagement looks the same. The right method depends on what you want tested and how much knowledge testers should have going in. Five approaches cover most engagements: external, internal, blind, double-blind, and targeted testing, each simulating a different attacker perspective and level of insider access.

Here's a closer look at each one.

External testing

External testing simulates an attacker with no prior access, probing your organization purely from the outside. Testers target internet-facing assets: websites, APIs, mail servers, and any exposed infrastructure a stranger could find and attack without ever setting foot inside your network.

This method answers a specific question: what can someone with zero insider knowledge break into using only publicly available information? It's often the starting point for organizations building out a security testing program, since perimeter weaknesses are usually the first thing real attackers probe.

Internal testing

Internal testing starts from inside the network, simulating either a malicious insider or an attacker who has already breached the perimeter through phishing or another entry point. Testers assess what damage is possible once inside the environment.

This approach matters because most breaches don't stop at the front door. Once an attacker gains a foothold, lateral movement, privilege escalation, and access to sensitive systems become the real risk. Internal testing shows exactly how far that access could realistically spread.

Blind testing

Blind testing gives testers minimal information going in, similar to what a real external attacker would have. They rely on reconnaissance and publicly available intelligence rather than internal documentation handed over by the client.

The organization's security team knows a test is happening, but doesn't share internal details upfront. This produces a more realistic picture of what an actual adversary could accomplish, since testers have to work for every piece of information the same way a real attacker would.

Double-blind testing

Double-blind testing takes blind testing a step further. Neither the pentesters nor most of the organization's staff, including the security operations team, know the test is happening in advance.

This method evaluates something the other approaches can't measure well: how your detection and incident response actually perform under real conditions. If your security team doesn't notice the activity at all, that's a vulnerability in itself. Double-blind engagements require careful coordination with leadership beforehand to avoid unnecessary panic.

Targeted testing

Targeted testing, sometimes called a "lights on" test, involves full collaboration between the pentester and the client's IT or security team. Both sides know the test is happening and often work through it together in real time.

This approach trades some realism for speed and educational value. It's useful when the goal is to train internal teams, quickly validate a specific control, or get fast feedback on a known area of concern, rather than simulating a full-scale, unannounced attack scenario.

Common Penetration Testing Mistakes

Treating a pentest as a one-time compliance checkbox is the most common mistake. Attackers don't stop looking for new ways in after your audit closes, and neither should your testing program.

Another frequent gap is scoping too narrowly, testing only the login page or a handful of features while leaving the rest of the application unexamined. Skipping retesting is just as costly. A vulnerability that's reported but never confirmed fixed isn't actually resolved, no matter how detailed the original report was.

Relying solely on automated scanners is another trap. Scanners miss business logic flaws that require a human tester's judgment. Failing to give testers proper context about how the application is actually used often means the most damaging, real-world attack paths never get tested at all.

FAQs

Here are the questions that come up most often about penetration testing.

What are the benefits of penetration testing?

Penetration testing uncovers real, exploitable vulnerabilities before attackers do, going beyond what automated scanners catch. It validates whether your security controls actually hold up under attack, supports compliance requirements such as SOC 2 and ISO 27001, and provides enterprise buyers with concrete proof that your application can be trusted with their data.

Why are penetration testing phases important?

Each phase builds on the last. Skipping reconnaissance or threat modeling means testers miss the business-logic context needed to uncover deeper flaws. Skipping retesting means you never confirm a fix actually worked. Every phase closes a specific gap, and removing one leaves blind spots in the final result.

What are the responsibilities of a penetration tester?

A penetration tester is responsible for safely simulating real attacks without causing damage, documenting every vulnerability with clear reproduction steps, communicating critical vulnerabilities immediately rather than waiting for the final report, and helping the client's development team understand exactly how to fix each issue correctly.

Conclusion

Our comprehensive penetration testing approach to security assessment can be delivered as a one-off engagement or continuously managed. Discover the 7 steps to comprehensive penetration testing for ensuring robust application security.

If this post has given you a clear picture of what a thorough penetration test should include, the practical question is whether your current or prospective vendor's process actually covers all seven steps or whether some are abbreviated, skipped, or handled through automation. See how Software Secured approaches web application penetration testing and what each phase looks like in our methodology.