Your Guide to Application Penetration Testing -PlutoSec - Cyber Security Canada
Eiusmod enim tempor incididunt aut labore et dolore magna aliua ruis nostrud exercitation ullamco laboris.
Application Penetration Testing
This post aims to deliver a detailed guide on Application Penetration Testing (AST) and address frequently asked questions about its significance. PlutoSec, recognized as the leading cybersecurity firm in Canada, is committed to providing expert insights into AST and its value.
This guide includes:
An introduction to application penetration testing
In today’s digital landscape, developing robust security programs is crucial for organizations to meet defensive security objectives and manage risks effectively. Whether an organization creates its own internal applications, outsources the development of web or mobile apps, or utilizes open-source software or libraries, Application Security Testing (AST) is essential for ensuring strong cybersecurity assurance. Even well-established software development firms with thorough source code review practices may benefit from having their products tested to minimize risk.
A vulnerability or malicious code within an application can enable an attacker to gain unauthorized access, escalate privileges, disrupt essential services, steal confidential information, encrypt critical data for ransom, or even destroy valuable data. This guide will explore the various types of AST, helping stakeholders understand their differences and determine the appropriate testing methods for their specific assets.
Who Will Gain from This Guide
C-level executives responsible for IT security (CISOs, CSOs, VPs of Security)
Senior management (CEOs, Business Owners, Business Executives)
Managed Service Providers (MSPs)
Cybersecurity Architects, Network Architects, and Network Administrators
What is Application Penetration Testing?
Application Penetration Testing (often referred to as “Application Pentesting,” “Application Security Testing,” or “AST”) assesses web, mobile, and native desktop applications to uncover exploitable vulnerabilities and safeguard against cyber threats.
In a **black-box test**, penetration testers have no prior information about the target application and attempt to exploit it as a real-world attacker would. This approach allows for evaluating the application’s security and the effectiveness of its environmental controls, such as web-server configurations.
In a **white-box test**, testers are given detailed information about the application’s internal workings, which may include the full source code for thorough analysis.
**Grey-box testing** falls between black-box and white-box testing, where testers receive partial information about the application to help verify specific security objectives, including resilience to insider threats.
Learn more about the distinctions between black-box, white-box, and grey-box penetration testing.
Software development follows a process known as the Software Development Life Cycle (SDLC), and the environment where this development takes place is called Development Operations (DevOps). The SDLC stages include Design, Build, Document, Test, and Deploy. Ideally, IT and application security considerations should be integrated throughout all stages of the SDLC and DevOps (DevSecOps). However, due to the complexities of software development and the need to develop software cost-effectively, bugs and vulnerabilities often make their way into the source code. Additionally, there is a risk of malicious code being intentionally planted by insiders. Application Penetration Testing (App Pentesting) addresses both inadvertent bugs and deliberate malicious code.
App Pentesting may also be necessary for older software applications, especially if they have not been previously tested or have undergone changes. In cases with high risk mitigation requirements, App Pentesting can be an ongoing process that continually seeks to bypass security measures, achieve exploitation, and enhance the security of the software product.
Given the numerous ways software applications can fail or be exploited and the various impacts of such failures, App Pentesting must approach the problem from multiple angles to uncover and address all potential points of failure.
Application Penetration Testing aims to identify, but is not limited to:
Why is Application Security Testing Essential?
In 2021, companies faced an estimated $6 trillion in damages from cybercrime. To mitigate these substantial risks, organizations are boosting their cybersecurity budgets and adopting more proactive measures to reduce their exposure. According to an IBM report, the average cost of a data breach rose to $6.75 million CAD per incident in 2021, up from approximately $4 million CAD in 2018. The repercussions of cyberattacks can include operational disruptions, damage to brand reputation, loss of business relationships, and significant fines or class action lawsuits.
In 2021, the average cost of a data breach amounted to $6.75 million CAD per incident.
Organizations of all sizes rely on software, and for modern enterprises, the security of these applications is crucial for operational resilience. Given the potential damage from a cyber breach, it’s essential for companies to adopt a proactive approach to cybersecurity by rigorously testing and verifying application security.
For companies using third-party applications, there is a significant level of trust placed in vendors or open-source development processes that are not directly managed. Given that vendors often face budget and resource constraints, security can sometimes be overlooked in favor of other priorities. Application Security Testing (AST) provides a higher level of assurance about the reliability of software applications.
Moreover, when offering software as a service (SaaS) — whether it’s a website, mobile app, or desktop application — it’s crucial to uphold the producer’s brand reputation. Users and customers rely on the security of the software, and any failure in security can damage brand trust, reduce profits, and drive users to seek alternatives.
How Long Does Application Penetration Testing Typically Take?
The duration and resource requirements for application penetration testing can vary greatly due to the diverse technologies, functions, and complexities of software applications. More complex applications with numerous features generally require more extensive testing than simpler ones. Additionally, the programming language and software technologies used in the application influence the necessary expertise, tools, and information gathering for an effective assessment.
The length of an Application Penetration Test is also influenced by the depth of testing and the level of assurance an organization needs to meet its risk management requirements. Black-box testing, which simulates a real-world attack environment, involves time-consuming manual information gathering. In contrast, white-box testing, where full details including source code are provided, allows for a thorough review but is also time-intensive.
Grey-box testing offers a balanced approach by combining some pre-provided information with the real-world simulation of a black-box test, achieving a middle ground in terms of efficiency and depth. Grey-box and white-box tests often include “credentialed” testing, where account credentials are provided to simulate insider attacks, which can enhance focus on critical aspects of the application and improve efficiency.
Conducting black-box and white-box testing as separate phases provides the most comprehensive security assurance but requires the most time and resources.
What Are the Various Types of Application Penetration Testing?
Web Application Penetration Testing
Web-application penetration testing involves evaluating the security of a website and its hosting infrastructure. This can be done through various approaches:
The general process of a web-application penetration test is:
A comprehensive web-application assessment should cover all aspects of the OWASP Top Ten to ensure adherence to IT security best practices. This includes testing API endpoints that the application depends on and evaluating the configuration and security of the underlying infrastructure. Key components to test include the server application (such as Apache, Nginx, or Microsoft IIS) and any exposed services (like SSH, SFTP, or SQL).
If multiple web applications are hosted on the same server, all should be tested. A breach in one application could potentially compromise all other hosted applications and their data.
Mobile App Penetration Testing
Many companies have developed mobile apps for both internal use and customer engagement. Mobile app testing encompasses evaluating the mobile version of a web application as well as native apps installed directly on iOS or Android devices. This testing includes similar methodologies to web-application testing, such as checking for vulnerabilities listed in the OWASP Mobile Top Ten, verifying adherence to best practices, and assessing API endpoints and infrastructure.
Native mobile apps, however, present unique security challenges. For instance, “rooting” an Android device or “jailbreaking” an iOS device grants administrative privileges and the ability to inspect file and memory contents of installed applications. Therefore, mobile app security testing should also evaluate how the app performs under these conditions, as such vulnerabilities could potentially expose credentials or source code.
Native Desktop Application Penetration Testing**
Testing native Windows, macOS, or Linux applications is crucial to ensure they are securely designed and to minimize risks such as unauthorized access, privilege escalation, or data manipulation. Typically, native desktop applications should be assessed for proper input sanitization, safe handling of system command execution, memory mapping, object deserialization, and secure implementation of application logic, including type-checking and variable assignment. Additionally, applications running with administrator or root privileges pose higher risks and should undergo more thorough testing.
Each operating system presents its own set of potential vulnerabilities, so the testing approach varies depending on the OS. For native Windows applications, it is essential to verify that service paths used to load built-in functions and DLLs are protected against being replaced with malicious versions.
Open Source Software Penetration Testing
Many applications leverage open-source software (OSS) libraries to streamline development, reducing both time and costs. Despite OSS being publicly available, there’s no guarantee that the code has been thoroughly vetted by security-conscious developers. Indeed, some open-source packages have been found to contain malicious code or vulnerabilities. Companies may also depend on fully-developed OSS applications for critical business operations.
To ensure the highest level of security assurance for applications that rely on open-source packages, it is crucial to include pentesting of these packages, including a source code review. This approach is becoming increasingly popular in the software development industry, with more developers, security analysts, and penetration testers collaborating to share threat intelligence related to OSS.
Dynamic Application Security Testing
Dynamic Application Security Testing (DAST) involves evaluating an application in its operational state and can be performed using white-box, grey-box, or black-box testing approaches. This dynamic analysis ensures secure access control management, prevents the exposure of sensitive data, verifies proper error handling, and assesses the application’s resilience against attacks. An advanced DAST technique, fuzzing, involves submitting invalid, unexpected, or random data to test the application’s robustness.
Static Application Security Testing
Static Application Security Testing (SAST) involves auditing a software application by examining its source code, making it a form of white-box testing. Automated tools for source code analysis can detect functions or packages that may pose security risks, but manual review of the scan results is essential for accuracy. These source code analysis tools are available for all popular programming languages and frameworks, including those used for iOS and Android mobile applications.
What is the Difference Between SAST and DAST?
Static Application Security Testing (SAST) involves manually inspecting the source code of an application to identify all forms of vulnerabilities. It is a type of white-box testing since testers are provided with the application’s source code for evaluation. Unlike other testing methods, SAST does not execute the code during the testing process. SAST is integrated into the Software Development Life Cycle (SDLC) to assess the security of software structures such as functions, classes, and APIs.
Dynamic Application Security Testing (DAST) involves testing an application while it is running on a production server or in a testing environment. This method is considered black or grey-box testing because testers do not have access to the application’s internal details. DAST can only be performed later in the SDLC when a working version of the application is available.
By combining static and dynamic code analysis, software engineers and third-party vendors can verify an application with a high degree of assurance.
What Needs to Be Tested?
The most important factors determining the scope of a testing engagement include the type of application being tested, the required level of risk assurance, and the unique risks posed by the application. The type of application (web, mobile, desktop, open-source, or proprietary) dictates which testing methodologies are appropriate. Regardless of the application type, all should be tested for IT security best practices, including authentication, exposure of sensitive information and files, secure error handling, secure input handling, known package vulnerabilities, and exposed services and API endpoints.
The required degree of risk assurance will influence the depth of testing and the consideration of advanced testing procedures. Greater emphasis should be placed on testing systems, features, and functions that present a higher risk. Examples include payment processing features and critical operational and business logic. A risk assessment of the application’s unique purposes, business operations, design, and components will also guide how penetration testers should allocate their resources.
What Are the Differences Between Application Penetration Testing, DevSecOps, and Threat Modeling?
Application penetration testing is not the only method for enhancing the security and resilience of applications. DevSecOps and threat modeling are two other key cybersecurity processes that are important to understand and compare to application penetration testing.
Development Operations (DevOps) is a set of operational practices related to the Software Development Life Cycle (SDLC) aimed at improving the productivity, quality, and efficiency of software development. DevSecOps focuses on integrating security into the DevOps process, thereby enhancing the security of the final application. While DevSecOps may include Application Security Testing (AST), AST can also be used independently of DevSecOps. For instance, AST may be part of a corporate risk management or vulnerability management program if an organization outsources application development and needs to verify its security.
Threat modeling is a process that identifies contextual risks within an organization’s IT operations by modeling potential cyber-attacks. This approach supports a “Secure by Design” methodology. Threat modeling highlights the most critical security threats, attack vectors, and vulnerabilities, allowing for prioritized remediation and efficient allocation of defensive resources. If a threat model identifies a particular application as high-risk to business operations or sensitive data exposure, mitigation strategies may include AST to ensure that these critical applications are properly secured.
What is the OWASP Top Ten?
The OWASP Top Ten is a ranked list of the most critical web application security vulnerabilities, ordered according to the current web-application threat landscape. It serves as a fundamental checklist of security concerns for security teams during the design and development phases of an application, and as a guide for penetration testers. The list also provides a common terminology for security analysts to communicate effectively. Updated every three to four years, the list reflects changes in the web application threat environment.
In addition to the OWASP Top Ten Web Application Security Risks list, OWASP also maintains top ten lists for APIs (OWASP API Security Top 10), mobile applications (OWASP Mobile Top Ten), and cloud applications (OWASP Cloud-Native Security Top Ten).
For reference, here is the current OWASP Top Ten Web Application Security Risks list:
Broken Access Control
Cryptographic Failures
Injection
Insecure Design
Security Misconfiguration
Vulnerable and Outdated Components
Identification and Authentication Failures
Software and Data Integrity Failures
Security Logging and Monitoring Failures
Server-Side Request Forgery
See more information about the OWASP Top Ten.
How Frequently Should Application Security Tests Be Conducted?
Regularly scheduling Application Security Tests (AST) is crucial for effectively managing an enterprise security program. The term “exposure time” refers to the period between tests during which changes to an application may introduce new vulnerabilities. While large enterprises might have continuous AST programs, organizations without such a program should conduct tests before an application’s release, before major or minor updates, and after other significant changes.
Organizations might be legally required or need to comply with industry standards to enhance their overall security posture. For instance, financial applications handling payment card data must adhere to PCI-DSS, which mandates penetration tests every three months or following significant changes. Similarly, SOC-2 Type 2 requires continuous attestation of IT security compliance and a penetration testing program aligned with a business’s operational and risk objectives.
When considering a merger or acquisition (M&A), it is also advisable to request information about AST frequency, reports, and remediation activities. This due diligence can offer valuable insights into the risk management practices and security posture of potential partners.
What Is the Cost of Application Penetration Testing?
The cost of an application penetration test can vary widely based on the scope and complexity of the engagement. Typically, a professional-quality application penetration test ranges from $10,000 to $60,000.
Key factors influencing the cost include the complexity of the target application (whether it is a web application, mobile app, or desktop app), the type of testing performed (SAST or DAST), the extent of manual testing required, and the duration of the engagement. These factors are discussed and agreed upon between the organization and the penetration testing provider before testing begins.
Focusing on a smaller set of assets or providing detailed information upfront can help reduce costs. Organizations considering the value of penetration testing might start with a narrowly scoped test to evaluate the benefits it offers.
The Return on Security Investment (ROSI) metric is used to measure the ROI of penetration testing. ROSI is a specialized ROI calculation that compares the total costs avoided from potential security breaches to the expenses incurred from the penetration testing itself.
A general form of the ROSI equation is:
The ROSI equation is:
ROSI = (Cost of security breach avoided – Cost of prevention) / Cost of prevention
For instance, if your company anticipates avoiding a minor security breach costing $100,000 over the next year, and the penetration testing engagement costs $10,000, the ROSI calculation would be:
ROSI = ($100,000 – $10,000) / $10,000 = 9
This means the return on security investment would be nine times the cost of the penetration testing.
This indicates that the return on security investment would be nine times the cost of the penetration testing.
What Does a Report Include?
PlutoSec provides a professional, tailored report for each client, detailing the application assessment comprehensively. Each report includes an executive summary that outlines the assessment’s goals and scope, highlights discovered security flaws, and assesses the application’s overall security posture.
The report’s body covers the methodologies employed during testing, technical findings with steps to reproduce, collected evidence, and remediation information for any exploited vulnerabilities. It concludes with strategic and tactical security recommendations specific to the tested application, and includes informational appendices when necessary.
Who Will Conduct This Test?
The role of a pentester, also known as an ethical hacker, is a specialized IT security position that demands advanced training and certification. Ethical hackers can be either generalists, with broad knowledge of penetration testing techniques, or specialists, with deep expertise in specific aspects of pentesting. Specialists might focus on particular exploitation frameworks, protocols, operating systems, or types of exploits.
The OSCP (Offensive Security Certified Professional) is a globally recognized and leading certification for ethical hacking, offered by Offensive Security. While Offensive Security provides several certifications, the OSCP is the most comprehensive and well-regarded. At PlutoSec, all pentesters are highly trained ethical hackers holding advanced industry certifications, with a minimum requirement of the OSCP certification.
Although the OSCP is the minimum certification required at PlutoSec, many team members pursue additional certifications to further enhance their expertise, including:
This enables our team of OSCP-certified penetration testing professionals to showcase industry-leading, comprehensive hands-on expertise in penetration testing.
How to Choose a Penetration Testing Provider?
Outsourcing penetration testing offers several advantages, with the primary benefit being that fresh perspectives on a target environment can reveal potential security weaknesses that an internal security team might overlook. Internal teams can develop assumptions and blind spots that a motivated and specialized pentesting team is less likely to have.
While many internal enterprise security programs rely on automated scanning tools to detect known vulnerabilities and misconfigurations, these tools cannot identify all vulnerabilities. Over-reliance on automation can lead to a false sense of security, making it crucial to assess a cybersecurity firm based on their capability to perform advanced manual testing techniques.
The rise in ransomware has heightened the potential value of a cybersecurity breach, attracting highly skilled threat actors who develop custom exploits and master various cyber-attack strategies. A professional penetration testing team, with its specialized knowledge, skills, and tools, can simulate a broad range of realistic attacker tactics, techniques, and procedures (TTPs), providing stronger security assurances.
When choosing a penetration testing consultant, consider factors such as their reputation, trustworthiness, size, experience, and professionalism. Evaluate their certification status and specialized skills relevant to your organization’s environment.
What Sets PlutoSec Apart from the Competition?
Exceptional value and highly cost-effective
While our engagement prices are comparable to those of our competitors, we offer a comprehensive range of manual testing services that many of them do not provide. Automated testing is just the initial phase of a penetration testing engagement, and manual testing is essential for uncovering all security gaps and delivering the highest level of risk assurance.
Expert testers, all of whom hold at least an OSCP designation
At PlutoSec, we take a distinctive approach to talent acquisition. Our hiring process requires candidates to have at least an OSCP certification and to complete a rigorous 72-hour hacker challenge. Once hired, our penetration testers undergo continuous skills training and practical evaluations.
Our ethical hacking team at PlutoSec exceeds the expertise of our competitors. Firstly, many of our competitors do not require the OSCP certification. Secondly, our team of highly skilled ethical hackers employs an industry-leading methodology to uncover vulnerabilities and weaknesses that are often missed by traditional testing methods.
At PlutoSec, we thoroughly understand each in-scope component and its role within the overall system architecture. We customize our approach for every environment we assess, going beyond the industry standard of merely running automated software scans.
Our reporting methodology adopts a thoughtful narrative approach. Rather than providing only a technical description of the issues, we illustrate the contextual business impact of our findings. This narrative explanation highlights key takeaways and offers deeper insights into your organization’s cybersecurity posture.
Automated tools, such as software scanners, are insufficient on their own and must be complemented by extensive manual analysis and testing. A thorough penetration testing process aims to identify logical vulnerabilities and explore all possible security scenarios. Automated testing constitutes only 5% of our work, while the remaining 95% involves manually simulating real-life attacks.
At PlutoSec, we have developed a comprehensive foundational methodology and continuously enhance our cyber-threat intelligence (CTI) and skills. Our methodology not only evaluates the target environment but also examines exploitable attack vectors that industry standards may overlook, all without affecting pricing.
Learn more about PlutoSec’s Application Penetration Testing Services.

Empowering engagement through meaningful dialogue.
visit us, phone, or email for personalized assistance.
- +1 (905) 367-6038
- Contact@plutosec.ca
- 335 Yonge St, Toronto, ON M5B 2L3