What is Penetration Testing? [A Complete Guide]

Being a business leader comes with the greater responsibility of ensuring that your enterprise, applications, and digital assets are secure from threats.

Penetration testing aka pentesting is a proactive approach to finding and fixing vulnerabilities before the bad actor exploits them. It involves ethical hackers simulating real-world like cyberattacks on your enterprise infrastructure and assets towards finding possible ways in which an attacker can cause harm to your business operations and reputation through data theft or disruption.

Being proactive and controlled in nature, it measures the effectiveness of security measures implemented by your team towards ensuring it is functioning as intended without any security gaps.Penetration testing also helps to measure the effectiveness of the defenses.

Still why penetration testing is very much important for organizations to conduct periodically?

Well, this blog is intended to provide you with the expert opinion our team gathered compiled as a penetration testing guide for your business benefits.

What is Penetration Testing or Pen Testing?

Currently the world is experiencing a hypersonic shift in technology that too at an unprecedented rate. What used to take decades in the past is now happening in a few days or weeks.

With all these, cyberattacks are also being more and more sophisticated and frequent than ever, and companies in high-risk industries including financial services, healthcare, and SaaS (Software as a Service) are becoming the favorite target for the threat actors.

For these sectors of enterprises, penetration testing is never just a mere tool for meeting the stringent compliance requirements, but a most wanted asset for their business which helps in many ways.

Be it securing sensitive data, maintaining customer reputation, or ensuring continuity of the business, penetration testing is nothing mere but a necessity.

It is a systemic technique of periodic evaluation where the penetration testers mimic the techniques, tactics, and procedure as a malicious hacker in a controlled manner with proper authorization from you authorities aligning to the business requirements and global standards.

Penetration testing is never about just getting vulnerabilities in your system fixed at the earliest. It also covers different aspects and principles of building resilience against dynamic cyber risk landscape in favor of your business and its growth.

Types of Penetration Testing

When it comes to classifying penetration testing, it can be based on various categories. Based on infrastructure, main types are:

1. Network penetration testing

Components such as firewalls, routers, switches, and wireless networks are evaluated by the penetration testers with a focus to identify the vulnerabilities, misconfigurations, outdated software components, or weaker protocols.

The key areas focused in the penetration test include:

• Misconfiguration in firewall rules
• Strength or default credentials
• Weakness of VPN implementation
• Possibilities of man-in-the-middle (MITM) vulnerabilities

2. Web application penetration testing

Web applications are the favorite target for adversaries due to its wider usage by the majority of businesses across the globe. Penetration testers simulate attack on this infrastructure checks for common, recently emerged, and specific vulnerabilities in its infrastructure. The common vulnerabilities found in the web applications are SQL injection, cross site scripting, and insecure API endpoints.

And the key areas that a penetration tester focused during the test include:

• Validation of user input
• Check for authentication and session management
• Threats related to business logic
• Security measures in API

3. Mobile application penetration testing

Mobile application penetration testing is the practice of identifying weaknesses in an iOS or Android mobile application's security measures. The goal is to identify, prioritize, and resolve weaknesses prior to being maliciously attacked by attackers or scripts.

Backend APIs, authentication and authorization systems, improper session handling, filesystem permissions, communications between processes, and unprotected storage of information on the cloud and device are all commonly examined in this technique.

The key focus areas in mobile application penetration testing are:

• Sensitive information storage
• Data transfer through insecure network
• Possibility of reverse engineering and tampering
• Access control and permission issues

4. Social engineering testing

Human resource is the most important asset for any business and the weakest too. Social engineering is the tactic of manipulating people within or related to the organization or business to act as per the intent of the bad actor. If fallen to the prey of the adversary, even a lower level employee can be the front door opener to a catastrophic cyber incident like data breach or takedown of the entire infrastructure.

Social engineering testing is the technique of conducting penetration tests to evaluate susceptibility of employees to manipulation through various attack techniques such as phishing, pretexting, or baiting. With this, you will be able to understand the security awareness within the organization towards improving or making necessary changes.

They key techniques in the test include:

• Simulating spear phishing
• Check for physical baiting
• Vishing test
• Smishing test

5. Physical penetration testing

Physical penetration testing identifies holes in an organization's physical security systems and simulates how a real attacker would attempt to get access to restricted places or information evading physical controls, surveillance, and on-site security measures.

It could involve the use of social engineering tactics (such as pretending to be one of the staff members), unauthorized access to restricted places, or theft of company assets.

This is accomplished by quietly infiltrating through a back entrance, portraying themselves and fitting in with authorized personnel, or seizing the opportunity of distraction such as fire alarm or loud alerting sound.

In this assessment, the penetration testers primarily check for:

• Biometric system security
• Placement of surveillance camera and its blind spots
• Physical locks and barriers
• Response to adversaries of security personnel

What is Black Box, White Box, and Grey Box Penetration Testing

Based on the prior information given to the penetration tester, scope and the nature, penetration testing can be classified into three, which are as follows.

Black box penetration testing

No prior additional information about the target system is given to the penetration tester in this methodology. This is to gain insights on the exact simulation of an external bad actor in time of an incident.

The ethical hacker must discover vulnerabilities through all possible manners and exploit them without any access to internal details. This is ideal for testing perimeter defenses including intrusion detection systems, firewalls, and public-facing applications.

This provides an unbiased result and is time-consuming compared to other tests. However, it may not completely address all the deeper vulnerabilities in the system.

White box penetration testing

Contrary to the previous one, in white box, the penetration tester is given all the information and full access to the target system details such as architecture, source code, configuration, and reports.

Comprehensive evaluation of both the internal and external vulnerabilities are possible with this approach. It simulates how an insider or highly informed attacker can cause issues. It primarily focuses on the code-level issues, misconfigurations, and flaws in architecture.

It is faster in comparison to black box testing and ideal for securing complex systems, older infrastructures, or critical applications. However it might not always be able to understand how a bad actor would act.

Grey box penetration testing

It is a hybrid approach of black box and white box penetration testing, where the testers are given limited-required information about the target system prior. It can be partial documentation or credentials.

This balances the benefits of both approaches which are efficiency and realism to real world attack simulation.

The tester primarily focuses on areas that can be assessed with the available information and escalates to higher levels. It is efficient for focused areas and requires precise scoping for increased effectiveness of the outcome.

Manual vs. automated penetration testing

Manual penetration testing is conducted utilizing human knowledge, experience, creativity and instincts. Critical thinking and strategic investigation capabilities. It is considered the best for businesses in need for assessing vulnerabilities related to business logic flaws, and complex attack vectors.

In comparison to automated penetration testing, it is more time consuming and costly. However, sophisticated threats including chaining exploits and multi-layered defense bypass can be detected supported by features of context aware testing.

In contrast, automated penetration testing uses pre-instructed and trained software tools with specified case scenarios for scanning systems for vulnerabilities and misconfigurations. It is effective for higher level scans for identifying common known vulnerabilities and is best for enterprise-level testing or periodic testing.

Even though it is faster and less expensive, you cannot rely on identifying complex vulnerabilities since it relies on predefined test cases. Also, it often fails to notice subtle vulnerabilities along with higher chances of generating false positives.

Difference between Manual and Automated Pen Testing

Indeed both manual and automated penetration testing has its own benefits. However, a manual pentest has its own leverage when it comes to the quality of the result, coverage on the blind spots, controllability of the test, and the ability to differentiate between threats which need real-human contextual understanding.

Penetration Testing Methodology

To ensure thorough evaluation of the security posture of your assets, the penetration testers often follow structured methodologies. Better coverage, comprehensiveness, consistency and effectiveness can be ensured with it and following are a few of the globally accepted ones.

• OWASP Testing Guide
• NIST Penetration Testing Methodology (SP 800-115)
• PTES (Penetration Testing Execution Standard)
• OSSTMM (Open Source Security Testing Methodology Manual)
• CREST Penetration Testing Guide
• ISSAF (Information Systems Security Assessment Framework)
• PCI DSS Penetration Testing Guidelines
• MITRE ATT&CK® Framework

In common they all follow the test outline which starts from scoping and goes through the steps of reconnaissance, vulnerability assessment, penetration testing and documentation.

1. Scoping

Boundaries of the whole assessment, its objectives, and rules are defined in this initial phase with the legal consent of your business authorities. It involves understanding the business priorities and requirements, potential risks with the test, and legal and ethical guidelines along with signed agreements.

They are non-disclosure agreement (NDA), master service agreement (MSA), rules of engagement (RoE), liability waiver (or “Get Out of Jail Free” Agreement), authorization letter, data handling agreement, and service level agreement (SLA).

Get out of jail free letter is a document signed by enterprises before test which protects penetration tester from legal troubles.

2. Reconnaissance

Once necessary approvals and details are shared, the penetration tester gathers information about the target asset as much as possible using passive and active methods.

Open-source intelligence (OSINT) research is conducted to find publicly available information and tools such as Nmap and Shodan.io are used to gain details about services and ports which are exposed.

3. Vulnerability assessment

Once necessary data about the target asset is collected, misconfigurations and vulnerabilities are assessed using available and customized tools to the scenario. The identified threats are then prioritized based on its severity, exploitability, and business impact

Different layers of technology are targeted which include hosts, networks, or application layers.

4. Penetration testing

Once the target is assessed, the penetration testers conduct real-world attacks to check for the depth of vulnerability and its impact on the application and your business. Possibilities of privilege escalation or lateral movements are also tested in this phase to understand the response capabilities of the environment.

5. Documentation

All the findings are compiled into a comprehensive report in the end which primarily includes the summary of all the vulnerabilities with its business impact and clear actionable remediation recommendations.

Detailed technical information such as screenshots and PoC (Proof of Concept) of the exploits, and executive summary for non-technical stakeholders are also included in it.

6. Retesting

Expert human support will be provided to your team for best remediation of the vulnerabilities found since security is always a shared responsibility. Once they are fixed, complementary retests shall be conducted to ensure watertight security and to find any vulnerabilities that emerged in this short time between.

Benefits of Manual Penetration Testing

AI is a trend in recent times. However, till present, manual penetration testing boasts its ability to go beyond automated scanning in many aspects.

Starting from its ability to identify more complex security gaps in your assets such as business logic errors and chained threats. It is considered more reliable when in need for deeper validation towards ensuring compliance requirements in both paper and in practice.

Manual penetration testing helps flag vulnerabilities based on its impact by understanding its business context of the organization’s architecture and processes. Also, since it mimics real-world attack more practically, helping to evaluate the effectiveness of incident response procedure, find loopholes in monitoring, detection, and response functions which automated might overlook.

When Should You Perform Penetration Testing?

Penetration testing helps you to address vulnerabilities within your organization’s applications, systems, and infrastructure. However there will be times where your business priorities shall be focused on other important operations. They can be anything from development of an important feature for your application, migration process, to budget constraints.

As per expert opinions, following are the key scenarios when it is better to perform penetration testing with priority.

1. Pre-release phase of application or service

You might feel it is better to wait until a stable version of the application is released to start thinking about conducting penetration testing.

However, being prevention better than cure, securing your application from the design phase or at least along with the development is considered the best as soon as some of the fundamental features are functional.

This is often referred to as the shift-left security approach. This gives a solid foundation and makes ensuring resilience more easier while preventing highly time consuming security patching processes.

2. After system upgradation or migration

Often it is more viable to secure new applications once it is implemented than an obsolete or going to be no longer used. However, system upgrades, migration, or changes in infrastructure may bring in new vulnerabilities which penetration testing addresses precisely.

Performing penetration tests after implementing these changes helps your enterprise to find issues in configurations and address new attack surfaces which were introduced during the upgrade.

3. To comply with regulatory standards

Usually penetration testing is conducted on a recurring basis which is usually on a quarterly, semi-annually, or annually basis. This helps to maintain a strong security posture through resilience to even latest threats and thereby fostering a security-first culture.

4. On a regular basis

Usually penetration testing is conducted on a recurring basis which is usually on a quarterly, semi-annually, or annually basis. This helps to maintain a strong security posture through resilience to even latest threats and thereby fostering a security-first culture.

Conclusion

Cyberattacks are getting more advanced with the growth of technology and hence its increase in frequency. Penetration testing helps to determine the effectiveness of defenses implemented in your organization.

The need to secure sensitive data, maintain consumer reputation, and ensure business continuity is a necessity and never an additional task in the todo list as it used to be considered to be.

With UprootSecurity, being proactive towards ensuring threat resilience is no longer a super complex mission for your enterprise. The pay-per-vulnerability pricing model and the resource pool of industry expert penetration testers make it a win for your organization in hunting down the loopholes profitably.