Dynamic Analysis on iOS (Pre-iOS 17) Using Windows – A Practical Guide

Penetration testing iOS applications without macOS can be tricky, especially if your device is running iOS 16 or lower. Apple imposes strict security measures, restricting system access and sandboxing applications, but dynamic analysis is still possible on Windows using sideloading techniques and runtime manipulation tools.

This guide focuses on Windows-based dynamic analysis for iOS apps using Frida, Objection, and AltStore, offering hands-on techniques for testing security vulnerabilities without macOS or jailbreaking your device.

🔹 Why Perform Dynamic Analysis on iOS?

Static analysis (reverse engineering an app’s code) is useful, but dynamic analysis allows testers to interact with applications in real-time, intercept API calls, modify function outputs, and test authentication mechanisms while the app is running.

If your iPhone runs iOS 16 or lower, you can bypass restrictions and conduct real-time security testing using tools that don’t require a jailbroken device.

🛠 Essential Tools for Windows-Based Dynamic Analysis

Windows users can set up an effective iOS security testing environment without macOS using the following tools:

1️⃣ AltStore – Sideload Apps Without Jailbreak

Since Apple prevents direct app installations outside the App Store, AltStore provides a reliable sideloading method.

✔ Install apps for penetration testing (like DVIA-v2)
✔ Doesn’t require a developer account
✔ Works for non-jailbroken iOS devices

🔗 AltStore Installation Guide

2️⃣ Frida – Dynamic Hooking & Runtime Manipulation

Frida is a powerful framework for interacting with running iOS apps. It allows testers to trace API calls, modify function behavior, and extract sensitive data.

✔ Hook into running iOS processes
✔ Modify authentication methods dynamically
✔ Bypass security measures like Touch ID

Installing Frida on Windows

Run the following command in Windows PowerShell:

pip install frida-tools

Verify installation:

frida --version

To connect Frida to your iOS device via USB:

frida -U -n Safari -i

3️⃣ Objection – Automating Runtime Manipulation

Objection simplifies Frida usage by providing automated runtime manipulation commands.

✔ Identify insecure storage methods
✔ Modify authentication and return values dynamically
✔ Extract hidden data

Installing Objection on Windows

pip install objection

Example command to modify login validation dynamically:

objection --gadget DVIA-v2 explore
ios hooking set return_value "[LoginValidate isLoginValidated]" true

🔗 Objection Cheatsheet

📡 Connecting iOS to Windows for Dynamic Testing

To interact with running iOS applications from Windows, follow these steps:

Step 1: Pair Your iOS Device

Pairing your iPhone with Windows allows Frida and Objection to interact with apps.

idevicepair pair
ideviceimagemounter -t Developer DeveloperDiskImage.dmg DeveloperDiskImage.dmg.signature

or verify connection:

ideviceimagemounter -l

Step 2: Listing Running iOS Processes

To trace an application using Frida, first list all running processes on your iPhone:

frida-ps -Ua

This enables testers to attach Frida to a specific app for dynamic analysis.

Step 3: Hooking iOS Functions for Analysis

Use Frida to monitor login functions in DVIA-v2 (a vulnerable iOS app for security testing).

frida-trace -U -n DVIA-v2 -i "*login*"

This command hooks into login-related functions, allowing testers to modify authentication checks dynamically.

🔐 Dumping Keychain Data on iOS (Without macOS or Jailbreak)

Many iOS apps store passwords and tokens inside Keychain, making it a prime target for security testing.

Extracting Keychain Data with Frida

frida -U -n KeychainDump -e 'Keychain.dump()'

Check out this detailed OWASP guide for Keychain security analysis:
🔗 OWASP iOS Keychain Testing

🚀 Wrapping Up: Dynamic Analysis on iOS Without macOS

Even if your iOS device runs version 16 or lower, and you only have Windows, you can still perform in-depth security testing using AltStore, Frida, and Objection. These tools allow real-time analysis, function hooking, and authentication bypass techniques without needing a MacBook or jailbreaking your iPhone.

Want to dive deeper into iOS penetration testing? Check out these resources:
📌 DVIA v2 Hands-on Guide
📌 Frida & Objection Cheat Sheet