Penetration Testing: A Complete Guide

Penetration testing is a cybersecurity practice involving authorized simulated attacks to identify and address vulnerabilities in systems, networks, or applications.

It involves attempts to exploit vulnerabilities, which may exist in services and application flaws, operating systems, risky end-user behaviour, or improper configurations, to validate the efficacy of protection mechanisms and end-user observation of security policies.

Pen testing is also called ethical or white hat hacking because it is a simulated security attack authorized by your company.

The Benefits of Penetration Testing

Regular pen testing will ensure your defensive mechanisms protect against potential and actual threats. It will tell you whether your security systems are functioning as intended. Pen-testing is vital for every business as it helps to

Identify & prioritize security risks
Leverage a proactive defense approach
Intelligently manage vulnerabilities
Increase confidence in your security system
Discover the strength of existing security programs
Meet regulatory requirements

Different Types of Penetration Testing

Penetration Testing Types Based on Methods Used

Black Box Testing

Black Box Pen-testing is called External Testing or Trial and Error Testing. This test follows a real-world attack where the tester does not know the ins and outs of the application/ network/ system and will launch a brute force attack or a blind attack on the IT infrastructure.

White Box Testing

White Box Pen-testing, also known as Internal Testing or Structural/ Clear/ Glass Box Testing, is where the tester has root-/ admin-level access to and complete information about the systems/ networks/ applications that are to be tested, including the source code, IP address schema, OS details, etc.

The goal is to test the internal structure and strength of the systems/ networks/ applications against malicious insiders or outsiders who have stolen the credentials using a phishing attack.

With White Box Testing, you can understand if internal operations and modules are properly executed per specifications and detect logical, design, typographical, and syntax errors and misconfigurations within the infrastructure or environment. These require much more sophisticated penetration testing tools.

Grey Box Testing

Grey Box Pen-testing is where the tester is provided partial information about the systems/ networks/ applications, such as access to software code, system architecture diagrams, etc., to simulate an attack.

This type of test emulates a scenario where an external entity has obtained illegitimate access to infrastructure documents and traces how partial information access affects the target.

Pen-testing Types Based on Targeted Components/ Assets/ Areas

Network Pen-Testing

Network penetration testing identifies vulnerabilities, gaps, and loopholes in the network infrastructure, including networks, systems, hosts, and network devices like routers and switches. This testing combines local and remote assessments to cover internal and external access points.

It identifies exploitable entry points for internal and external attackers while assessing security risks for critical internet-facing assets and network infrastructure.

Commonly targeted areas include:

Firewall Configuration
Firewall Bypass
Stateful Analysis
SQL Server
IPS/IDS evasion
SMTP mail servers
DNS
Open ports
Proxy servers

Application Pen-Test

Application Pen-Testing is a complex, detailed, and targeted type of testing where strategic planning is necessary for greater effectiveness.

Here, globally accepted and industry frameworks simulate real-time attacks against applications to expose security lapses caused by insecure coding, development, and design practices.

Commonly targeted areas are:

Web applications and websites
Software
Mobile Apps
Internally/ externally developed programs
APIs
Applets and Scriptlets
Plug-ins
Frameworks
Browsers
Languages
Systems like CRM, HR systems, and SAP

Physical Penetration Testing

In physical penetration testing, also known as physical intrusion testing, the pen-tester attempts to breach physical security controls and barriers to gain access to critical assets and sensitive areas.

Common targets are:

Perimeter security
RFID and door entry systems
Intrusion alarms
Locks at physical locations
Cameras
Sensors and motion detectors
Mantraps
Human network at the organization

Social Engineering Pen-Testing

Through Social Engineering Pen-Testing, the human network at the organization is targeted through manipulation, trickery, phishing, scams, threats, tailgating, and dumpster diving by the tester to gain access to proprietary/ confidential information or physical access to assets.

Client-Side Pen-Testing

Client-side Pen-Testing/ Internal Testing is where the tester identifies potential security threats emerging internally from the organization and exploitable from the client end.

Common targets are:

Client-side Software
Web Browser
Content Creation Software (MS Office Suite, Photoshop, Adobe Page Maker)
Media players

Wireless Network Pen-Testing

This type of pen-testing seeks to identify vulnerabilities and weaknesses in the wireless devices used on the client side. For instance, tablets, smartphones and notebooks. These tests also include wireless protocols, access points, and admin credentials.

5 Signs That It’s Time for Pen-Testing

1. Your service is going live/ into production

IT/ development teams often work under impossible deadlines and push out applications. Businesses must assess the security of their systems/ services pre-deployment.

Remember that penetration tests must be conducted before the systems go live/ into production when it is no longer in a constant state of change.

2. You have made changes to infrastructure/ web applications

Significant changes to the infrastructure or web applications include:

Installation of new software/ infrastructure/ applications
Modifications to code
Old software being decommissioned
New third-party services onboarded
New physical office sites are being added to the network
Physical office relocation
Introduction of new IoT devices into the system
Network equipment changes

Such major changes to the IT infrastructure create vulnerabilities that automated scanners may overlook. With security penetration testing, organizations can identify any security loopholes/ misconfigurations or logical errors that may arise from such major changes.

3. You have applied security patches

Security patches are fixes to already released software with the intent to fix errors/ vulnerabilities/ security loopholes. Since patch information is publicly available, attackers tend to read up on and find ways to breach the patches and the patched vulnerability.

So, it is neither advisable to apply security patches across all devices the moment they appear without considering their impact nor is it wise to ignore security patches altogether.

Organizations must adopt a security-focused, strategic approach to security patches. They must test the patches securely before applying them across the entire IT environment.

With web penetration testing, organizations can prioritize critical areas to patch and ensure that the patch effectively secures the vulnerabilities.

4. You have modified policies

Changes in business policies and end-user policies may create vulnerabilities and logical flaws that cannot be detected by scanning tools and simple vulnerability assessments. Pen tests are vital to identify such misconfigurations and logical flaws.

5. Your industry is being regularly targeted

If you have been getting alerts about crafty and sophisticated cyber-attacks targeting your industry, it is time to conduct security penetration testing. This could be because of technological or regulatory changes in the industry or other factors that are causing the attack surface to widen.

The Types of Vulnerabilities Targeted in Pen Tests

Access Control Management

The testing determines the authentication and authorization concerning the access control given to the users per their organizational roles. The tester creates multiple user accounts across different roles to check privileges or restrictions assigned to the users.

Server Access Control

This testing finds out whether there are any open access points on the intra-network and inter-network of the organization. If any such open access is discovered, the tester checks for the same vulnerability from different devices.

Password Management

Password breaches can lead to identity theft or malicious activities. Manual application penetration testing can mitigate the risk to a significant extent. The testers check for weak password by using different combinations.

Session Management

While session management control eliminates the need to log in and out of sessions repeatedly, it is highly vulnerable to cyber hijack. Pen testers check whether cookies and tokens are secure enough in terms of session termination after login/log out scheduled lifetime or idle time.

SQL Injection

MOVEit is the latest attack in the SQLi family that has been hackers’ weapon of choice for more than two decades. We block 2M+ SQLi attacks on the AppTrana network each month.

SQL injection is one of the most dangerous and common web application vulnerabilities. Manual testing helps detect the entry points hackers can exploit to inject malicious SQL commands.

Penetration testing exposes other known OWASP top vulnerabilities and avoids massive disasters.

Ingress and Egress Entry Points

Ingress and egress points refer to the direction of network traffic. Ingress is the incoming traffic that enters the network boundary. Egress is the opposite –the outgoing traffic from the network boundary.

Hackers will use it to their advantage if the security parameters are not tight at both points. During manual security penetration testing, sensitive/confidential data is transmitted between the host and unauthorized/restricted networks to plug the vulnerabilities.

Manual penetration testing can catch many more flaws than those mentioned above. The decision of the test cases you want to execute depends on the complexity of the web application and the types of vulnerabilities you want to assess.

Web Application Penetration Testing Best Practices

Prepare the Pen Testing Environment

Web application pen testing should be performed on the production environment. While conducting the test directly on production, you should set specific limits for the pen testers. Also, schedule the test in a way that does not slow down the network response time for your organization and your clients.

The most important restriction is not to run a DoS attack simulation on production. If your pen test can’t be conducted in the production environment, prepare an environment identical to production and generate user accounts for the pen testers.

Build Attacker’s Personas

For better results, web-based penetration testing must be enacted realistically. While testing, you should put yourself in the shoes of the attackers’ persona. You must think and act like an actual cyber attacker, equipped with an advanced motive, goals, and skills. The motive is a vital element in structuring hacker personas.

Business or money advantage, revenge by an ex-business partner, culture or religious ideology, and peer recognition are possible motives.

Set Testing Boundaries Clearly

Everyone should remember that web app penetration testing is just a simulation, not an actual attack. Hence, the testing boundaries should be outlined as to:

Who will perform the test?
When should the test be conducted?
What is permissible and what can’t be done?
To whom should all reports and communications be sent?

Define Web Penetration Testing Methodology

When it comes to penetration testing best practices, pen test methodology is an imperative step for both external and internal pen testers.

The testing methodology is a set of security guidelines on which your web penetration testing should be conducted. Ensure the testing is aligned with industry-standard security frameworks and comprises automatic and manual advanced testing.

Some of the important pen testing methodologies & standards are:

Open Web Application Security Project (OWASP)
Penetration Testing Framework (PTF)
Open Source Security Testing Methodology Manual (OSSTMM)
Information Systems Security Assessment Framework (ISSAF)
Payment Card Industry Data Security Standard (PCI_DSS)

Launch Security Monitors Before

If you don’t want to waste your valuable manual pen-testing time, it is best practice to implement a security scanner or monitor. If you have web application monitoring to detect your basic issues and vulnerabilities, the pen testers do not need to spend their energy uncovering those issues.

Freeze Development in Penetration Testing Environment

The best practice of penetration testing is to test the application, not individual pieces of it. Pen testing will detect the vulnerabilities within the given settings. If you change that setting by adding new patches or packages or modifying hardware components, you won’t be able to get valid pen testing results.

Similarly, fixing the issue while testing is not advisable, though this is vital for some occasions.

Choose the Right Penetration Testing Tools

Plenty of pen-testing tools are available in the market – some are free to download and use, and some are vendors supplied. Selecting the right tool(s) depends mainly on your pen-testing environment.

If you’re confused about what makes the best penetration testing tool, here is our guide.

Decide Between In-house Testers and External Pen-Testing Services

You can get a lot of advantages from in-house pen testers if they have the skillset. Besides cost savings, the in-house team is more familiar with your application.

However, it is better to opt for specialized external web app penetration testing professionals to leverage more expertise and an out-of-box point of view. It also ensures organizational independence for penetration testing that provides best practices to the difference of opinion and a need by PCI compliance.

Top Reasons Why Manual Penetration Testing is Essential

Detect Vulnerabilities that Automated Scans May Miss

While automated scanners infuse speed and agility in identifying vulnerabilities and security misconfigurations, some vulnerabilities cannot be identified without manual pen tests.

For example:

Business Logic Flaws include price or other parameter manipulation, privilege escalation, business flow bypass, etc.
Chain Attacks
Insecure Direct Object Reference (IDOR) Flaw
Zero-day Exploits
DOM-based XSS

In all these cases, the vulnerabilities cannot be identified using universal approaches and automated tools owing to the complexity of the flaws. The expertise, unconventional thinking, and skillsets of certified and trusted security specialists are essential for identifying such vulnerabilities.

First Mover Advantage

Even critical vulnerabilities take over 100 days to be patched after detection. So, businesses must gain the first-mover advantage that penetration testing gives them to identify, patch, and fix vulnerabilities before cybercriminals can find them.

Understand How Vulnerabilities can be Exploited

Even though automated scanners and other tools identify vulnerabilities and misconfigurations, it is crucial to know how attackers can exploit them in real-time. This is made possible through penetration testing by trusted security experts.

Effective Risk Assessment

By gauging the impact of vulnerabilities and the probability of potential threats materializing, the cyber risks facing organizations are demonstrated by pen tests. Risks can also be prioritized based on the findings of a pen test.

Recommendations for Mitigation

Given that the identification of vulnerabilities is only a part of web application security, it must be followed by remediation and risk mitigation. The pen-tester provides detailed reports after penetration testing, along with recommendations and actionable insights to secure the application and strengthen security measures.

Compliance with Security Regulations

With the number of regulations concerning customer data and data security, pen testing will enable businesses to comply—for instance, GDPR guidelines, Payment Card Industry Data Security Standard (PCI DSS), etc.

Is Penetration Testing Essential for Your Business, Alongside a Vulnerability Scanner?

Yes. It is necessary. Web application security is not a one-time thing and must not be treated that way. It must be continuous, and businesses must proactively and consistently secure their web application.

Even with high-end security processes and infrastructure, there is a need to ensure no vulnerabilities and loopholes. Also, automation can only take businesses to a certain point in cybersecurity; nothing can replace human expertise and intelligence.

Therefore, certified security experts must do pen-testing as they can use the security testing tools best while leveraging automation and other technology to help businesses continuously detect, protect, and test their web application security and performance.

Indusface’s Web Application Scanner (WAS) is a comprehensive tool encompassing DAST, Malware Scanning, and Infrastructure Scanning, all within a single platform. This ensures the immediate identification of all vulnerabilities in one place, providing a detailed overview of your security gaps. Additionally, it includes manual penetration testing service for web applications, mobile apps, and APIs to pinpoint business logic vulnerabilities.

Indusface’s penetration testing suite is a well-rounded and sophisticated solution for all your penetration testing requirements. The Indusface security team guarantees zero false positives by manually exploiting vulnerabilities.

The resulting penetration test report is exceptionally comprehensive and remains user-friendly. You also benefit from top-notch expert support if your developers encounter challenges while addressing these issues.

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