iOS Application Penetration Testing Checklist [153 Test Cases in a Free Excel File]

Get Free iOS Application Penetration Testing Checklist [Excel file]

Apple’s recent release of iOS 16 for the iPhone brings important new security features. Despite the inherent security features of iOS, additional measures, techniques, and guidelines can be employed to fortify the protection of user data and ensure privacy.

Having previously covered the Android penetration testing checklist and security assessment, it is time to focus on iOS.

What is iOS App Penetration Testing?

iOS application penetration testing is a process of assessing the security of an iOS application to identify vulnerabilities and weaknesses that attackers could potentially exploit.

It involves systematically evaluating the application’s design, code, configurations, and implementation to uncover potential security flaws that may compromise the confidentiality, integrity, or availability of the iOS application and its associated data.

7 iOS Application Penetration Testing Techniques

During an iOS application penetration test, a pen tester employs various techniques, tools, and methodologies to assess the application’s security posture. This may include:

1. Static Analysis

Static analysis tools help identify security vulnerabilities in the application’s source code or binary without executing it. These tools can detect issues such as insecure coding practices, improper use of cryptographic functions, presence of backdoors, and hardcoded sensitive information. Additionally, static analysis can assist in identifying common vulnerabilities, such as buffer overflows, SQL injection, and cross-site scripting (XSS)

2. Dynamic Analysis/ Runtime Manipulation

Dynamic analysis entails running the application in a controlled environment to closely monitor and analyse its behaviour. This technique allows testers to capture runtime information, monitor API calls, intercept network traffic, and detect potential security weaknesses.

Runtime manipulation techniques involve modifying the application’s behaviour during execution. Method swizzling is a common technique to replace or intercept method calls dynamically. By altering the behaviour of specific functions, testers can analyse how the application handles different scenarios, identify insecure function calls, and bypass security controls such as certificate pinning or jailbreak detection mechanisms.

Dynamic analysis tools can uncover vulnerabilities related to authentication bypass, session management flaws, insecure data storage, and improper user input handling.

The pen tester should have access to diverse techniques, from basic LLDB debugging to advanced methodologies like dynamic binary instrumentation, code injection, and other malicious strategies to alter an iOS application during runtime.

3. Jailbreaking

Jailbreaking an iOS device provides testers with elevated privileges and access to system files, enabling them to perform more comprehensive security assessments. It allows for installing additional tools, modifying system settings, and monitoring system processes. Jailbroken devices facilitate the analysis of sensitive information, debugging of applications, and the exploration of file systems for potential vulnerabilities.

Jailbreaking techniques bypass the limitations and restrictions imposed by the iOS operating system on iPhones and iPads, allowing users to gain root access and install unauthorized applications and modifications. Here are some common types of jailbreaking techniques:

• Tethered Jailbreak: A tethered jailbreak requires the device to be connected to a computer every time it is rebooted or turned on. The jailbreak is applied temporarily, and the device will lose its jailbroken state if not connected to the computer.
• Untethered Jailbreak: An untethered jailbreak allows the device to remain jailbroken even after rebooting or turning it off. This jailbreak provides persistent root access, and the device does not require a computer connection to maintain its jailbroken state.
• Semi-Tethered Jailbreak: A semi-tethered jailbreak combines aspects of tethered and untethered jailbreak. It allows the device to function normally without a computer connection. Still, some jailbreak features may be turned off until the device is connected to a computer and the jailbreak is reactivated.
• Semi-Untethered Jailbreak: Like a semi-tethered jailbreak, a semi-untethered jailbreak allows the device to operate normally without a computer connection. However, certain jailbreak features may be temporarily disabled until the user launches a specific app on the device to reactivate the jailbreak.
• One-Click Jailbreak: This type involves using a simple and user-friendly tool or application that automates the jailbreaking process. Users can typically jailbreak their device with just a few clicks, making it more accessible to a broader audience.

4. Traffic Interception

Intercepting network traffic between an iOS device and the server helps identify potential security weaknesses. Testers can capture and analyse network packets using tools like Wireshark or Burp Suite. This iOS pen testing technique allows for examining requests and responses, detecting insecure transmission protocols, identifying sensitive information leakage, and analysing encryption mechanisms employed by the application.

5. Binary Analysis

Analysing the application’s binary code assists in understanding its internal workings and identifying potential vulnerabilities. Reverse engineering tools like IDA Pro or Hopper Disassembler can decompile, disassemble, or debug the binary code. This technique helps uncover hidden functionality, detect insecure library usage, identify cryptographic algorithms, and locate potential entry points for exploitation.

6. App Tampering or Bypassing Security Controls

In the iOS application penetration testing process, the tester will actively seek out and aim to neutralize or bypass any security measures implemented within the application itself. One of the primary targets for disabling or bypassing is anti-tampering measures. By bypassing these protections, testers can navigate more freely within the app, search for sensitive data, or escalate their compromise of the application.

Once tamper protection is disabled, the testers can make various unauthorized modifications, including altering the core binary or resources within the app bundle. They can also locate and modify properties files by changing key/value pairs stored in plists. These modifications include altering bundle IDs, configurations, preferences, and permissions or manipulating any values stored in plists, key/value pairs, or dictionary values.

Testers may perform these activities to assess the ease with which attackers could create clones or modified versions of the app and explore the possibility of repackaging or redistributing the app through alternative app stores.

7. SSL Pinning Bypass / MitM Attack   

An SSL pinning bypass is a technique employed by testers to evaluate the implementation and efficacy of this security measure. During iOS penetration testing, one of the key objectives is to evaluate the susceptibility of the app’s networking connections and trust mechanisms that facilitate communication with backend servers. Given the zero-trust nature of mobile app environments, there are numerous ways for testers to achieve this.

By conducting a Man-in-the-Middle (MitM) attack, the testers can replace the app’s digital certificate with their preferred proxy tool’s certificate (e.g., Charles Proxy, Burp Suite, Wireshark). This manipulation allows the testers to redirect the app’s traffic through their proxy, allowing them to analyze, modify, or further compromise the app.

Which Key Areas Does iOS Application Penetration Testing Cover?

When conducting iOS penetration testing, several key focus areas should be considered to ensure a comprehensive assessment of the iOS application’s security. Here are some critical focus areas:

Network Communication

Evaluate the security of network communication channels used by the application, including API endpoints, data encryption, and authentication mechanisms. Look for vulnerabilities like insecure network protocols, weak encryption algorithms, or improper certificate pinning implementation.

User Authentication and Authorization

Assess the effectiveness of user authentication and authorization mechanisms implemented within the application. Test for common vulnerabilities like weak password policies, improper session management, insecure storage of credentials, and privilege escalation opportunities.

Data Storage

Analyzing how an application stores sensitive data is crucial for identifying vulnerabilities. Review how sensitive data is stored on the device, such as personally identifiable information (PII) or authentication tokens.

Evaluate the capability of data encryption, secure storage mechanisms, and protection against data leakage or tampering. This analysis helps identify issues such as weak encryption, improper use of hashing algorithms, insecure storage of credentials, and leftover data traces after deletion.

Input Validation and Output Encoding

Check for input validation vulnerabilities, including issues like SQL injection, cross-site scripting (XSS), or remote code execution. Ensure user inputs are properly validated, sanitized, and encoded to prevent exploitation.

Secure Coding Practices

Assess the overall security of the application’s codebase, including identifying common coding vulnerabilities such as buffer overflows, integer overflows, or insecure use of third-party libraries. Review adherence to secure coding practices, including proper use of memory management, sensitive data handling, and code injection prevention.

Session Management

Evaluate how the application manages user sessions, including creation, expiration, and termination—test for vulnerabilities like session fixation, session hijacking, or insufficient session timeout settings.

Error Handling and Logging

Analyse how the application handles errors, exceptions, and logging. Check for sensitive information leakage through error messages or logs that could assist an attacker in identifying vulnerabilities or gaining unauthorized access. Know the impacts of excessive data exposure.

Compliance with Security Standards and Guidelines

Ensure the application complies with relevant security standards and guidelines, such as the OWASP Mobile Application Security Verification Standard (MASVS), Apple’s iOS Security Guidelines and and the OWASP Mobile Top 10. Verify if the application follows best practices for secure development, encryption, and privacy protection.

Broken Cryptography

Broken cryptographic algorithms or implementations can be a significant vulnerability in iOS applications. During mobile application penetration testing, assessing the strength and effectiveness of cryptographic mechanisms used within the application is essential.

• Assess the strength of passwords used for cryptographic purposes
• Verify whether the application uses deprecated or weak cryptographic algorithms to send or store sensitive data.
• Monitor Cryptographic Functions through Hooking
• Evaluate the length and strength of cryptographic keys used by the application
• Analyse the implementation of SSL/TLS protocols for secure communication between the application and backend servers.

API Testing

Mobile applications often interact with various APIs for functionalities like user authentication, data retrieval, or payment processing.

• Analyse how the application handles API requests and responses
• Verify the implementation of secure communication protocols (such as HTTPS)
• Assess authentication and authorization mechanisms
• Evaluate the validation and sanitization of user input to prevent common vulnerabilities like API injection or parameter tampering and OWASP API Top 10.

Explore the API Penetration Testing Checklist, comprising a comprehensive range of use cases to conduct a comprehensive API security assessment.

Third-Party Library Usage

Third-party libraries often introduce potential vulnerabilities and can be a target for attackers. Here are some factors for checking third-party library usage:

• Identify the third-party libraries used by the application and review their versions.
• Utilize vulnerability databases and security resources to search for any reported vulnerabilities associated with the third-party libraries.
• Determine if the application is regularly updated with third-party library developers’ latest patches and updates.
• Verify that the usage of third-party libraries complies with their respective licenses.

This iOS application penetration testing checklist lets you identify vulnerabilities, weaknesses, and potential attack vectors in your iOS infrastructure. This proactive approach enables you to address security gaps promptly, mitigate risks, and ensure the robustness of your iOS ecosystem.

Ultimately, a well-executed penetration testing checklist bolsters the overall security stance and fosters trust among users, clients, and stakeholders.

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