IOS Pentesting Tricks

SKILL: iOS Pentesting Tricks — Expert Attack Playbook

AI LOAD INSTRUCTION: Expert iOS application security testing techniques. Covers jailbreak vs non-jailbreak methodology, keychain extraction, URL scheme/Universal Links abuse, Frida/Objection runtime hooks, binary protection checks, and data storage analysis. Base models miss protection class nuances and AASA misconfiguration patterns.

0. RELATED ROUTING

Before going deep, consider loading:

• mobile-ssl-pinning-bypass for in-depth SSL pinning bypass (SecTrust hooks, SSL Kill Switch, framework-specific techniques)
• android-pentesting-tricks when also testing the Android version of the same app
• api-sec for backend API security testing once traffic is intercepted

Advanced Reference

Also load IOS_RUNTIME_TRICKS.md when you need:

• Frida recipes for iOS-specific hooks (ObjC class enumeration, method swizzling)
• Objection command reference for iOS
• Runtime hooking patterns and bypass templates

1. JAILBREAK VS NON-JAILBREAK TESTING

Non-Jailbreak Testing Setup

# Extract IPA from device
ideviceinstaller -l                    # List installed apps
ios-deploy --id <UDID> --download --bundle_id com.target.app

# Or use frida-ios-dump for decrypted IPA (jailbroken)
python dump.py com.target.app

# Sideload with Frida gadget (non-jailbreak runtime hooking)
# 1. Extract IPA, 2. Insert FridaGadget.dylib into Frameworks/
# 3. Re-sign with valid profile, 4. Install via ios-deploy

2. KEYCHAIN EXTRACTION

2.1 Keychain Protection Classes

2.2 Extraction Methods

# Jailbroken: keychain-dumper
/path/to/keychain-dumper -a              # Dump all accessible items
/path/to/keychain-dumper -g password     # Generic passwords only
/path/to/keychain-dumper -i              # Internet passwords

# Frida / Objection
objection -g com.target.app explore
> ios keychain dump
> ios keychain dump --json                # JSON output for parsing

# Frida script for keychain enumeration
frida -U -f com.target.app -l keychain_dump.js

2.3 What to Look For

3. URL SCHEME HIJACKING

3.1 Custom URL Scheme Discovery

# From IPA/app bundle — check Info.plist
plutil -p /path/to/Payload/Target.app/Info.plist | grep -A 10 CFBundleURLTypes

# Example output:
# "CFBundleURLSchemes" => ["targetapp", "fb123456789"]

3.2 Hijacking Attack

Scenario: Target app registers "targetapp://" for OAuth callback

1. Attacker app also registers "targetapp://" URL scheme
2. User initiates OAuth login in target app
3. OAuth provider redirects to targetapp://callback?code=AUTH_CODE
4. iOS may open attacker's app instead (non-deterministic scheme resolution)
5. Attacker captures OAuth authorization code

3.3 URL Scheme vs Universal Links Security

4. UNIVERSAL LINKS EXPLOITATION

4.1 AASA (Apple-App-Site-Association) Misconfiguration

# Fetch AASA file
curl -s "https://target.com/.well-known/apple-app-site-association" | jq .
curl -s "https://target.com/apple-app-site-association" | jq .

# Check for wildcard patterns (overly broad)
# Bad: "paths": ["*"]     ← captures ALL URLs
# Bad: "paths": ["/NOT *"] ← poorly written exclusion

4.2 Breaking Universal Links → URL Scheme Fallback

Technique: Force Universal Link to not open app, causing fallback to URL scheme

1. User long-presses link → "Open in Safari" (disables UL for that domain)
2. Redirect chain: domain A → domain B → target (UL breaks on redirect)
3. JavaScript redirect instead of 302 (UL only works on server-side redirects)
4. App not installed → URL scheme fallback → hijackable

5. RUNTIME MANIPULATION

5.1 Frida on iOS

# Connect to app on jailbroken device
frida -U -f com.target.app --no-pause

# Basic ObjC exploration
> ObjC.classes                                    # List all classes
> ObjC.classes.NSURLSession                       # Check if class exists
> ObjC.classes.AppDelegate.$methods               # List methods
> ObjC.classes.AppDelegate['- isLoggedIn'].implementation  # Read method

# Hook method and modify return value
Interceptor.attach(ObjC.classes.AuthManager['- isAuthenticated'].implementation, {
    onLeave: function(retval) {
        retval.replace(ptr(1));  // Force return TRUE
    }
});

5.2 Objection iOS Commands

objection -g com.target.app explore

# Keychain
> ios keychain dump

# Cookies
> ios cookies get

# Pasteboard
> ios pasteboard monitor

# Jailbreak detection bypass
> ios jailbreak disable

# SSL pinning bypass
> ios sslpinning disable

# Binary info
> ios info binary

# Hooking
> ios hooking watch class AppDelegate
> ios hooking watch method "-[AuthManager isAuthenticated]" --dump-args --dump-return
> ios hooking set return_value "-[AuthManager isJailbroken]" false

5.3 Cycript (Legacy but Useful)

// Attach to running app
cycript -p com.target.app

// Explore UI hierarchy
UIApp.keyWindow.recursiveDescription().toString()

// Find view controllers
[UIWindow.keyWindow().rootViewController _printHierarchy].toString()

// Call methods directly
[AppDelegate.sharedInstance isLoggedIn]  // → check return
AppDelegate.sharedInstance.isLoggedIn = true  // → modify

// Access singleton instances
var vc = choose(LoginViewController)[0]
vc.bypassLogin()

6. BINARY PROTECTIONS

6.1 Checking Binary Security

# PIE (Position Independent Executable)
otool -hv /path/to/binary | grep PIE

# ARC (Automatic Reference Counting)
otool -I -v /path/to/binary | grep objc_release

# Stack canaries
otool -I -v /path/to/binary | grep __stack_chk_guard

# Encryption (FairPlay DRM)
otool -l /path/to/binary | grep -A 4 LC_ENCRYPTION_INFO
# cryptid 0 = decrypted, cryptid 1 = encrypted

6.2 Decrypting IPA

# frida-ios-dump (preferred, jailbroken device)
python dump.py com.target.app
# Outputs: decrypted IPA in current directory

# bagbak (alternative)
bagbak com.target.app

# Manual via Frida
frida -U -f com.target.app -l dump_memory.js
# Dump decrypted binary from memory, replace encrypted section

6.3 Class-dump for ObjC Analysis

# Dump Objective-C class information
class-dump /path/to/decrypted/binary > classes.h
class-dump -H /path/to/decrypted/binary -o /tmp/headers/

# Search for interesting patterns
grep -r "password\|token\|secret\|apiKey\|isJailbroken\|isRooted" /tmp/headers/

7. DATA STORAGE ISSUES

7.1 Sensitive Data Locations

7.2 Inspection Commands

# On jailbroken device — app sandbox at:
# /var/mobile/Containers/Data/Application/<UUID>/

# Find app UUID
find /var/mobile/Containers -name "com.target.app" 2>/dev/null

# Check NSUserDefaults
plutil -p Library/Preferences/com.target.app.plist

# Check SQLite databases
sqlite3 Library/Application\ Support/Model.sqlite ".tables"
sqlite3 Library/Application\ Support/Model.sqlite "SELECT * FROM ZUSER;"

# Check for sensitive strings in all files
grep -r "password\|token\|bearer\|api_key" Documents/ Library/

8. TRANSPORT SECURITY (ATS)

8.1 ATS Exception Patterns

<!-- Info.plist — check for ATS exceptions -->
<key>NSAppTransportSecurity</key>
<dict>
  <!-- WORST: disables ATS entirely -->
  <key>NSAllowsArbitraryLoads</key>
  <true/>

  <!-- BAD: specific domain exceptions -->
  <key>NSExceptionDomains</key>
  <dict>
    <key>insecure-api.target.com</key>
    <dict>
      <key>NSExceptionAllowsInsecureHTTPLoads</key>
      <true/>
      <key>NSExceptionMinimumTLSVersion</key>
      <string>TLSv1.0</string>
    </dict>
  </dict>
</dict>

9. IOS PENTESTING DECISION TREE

Testing iOS application
│
├── Device jailbroken?
│   ├── Yes → full testing capability
│   │   ├── Keychain dump → ios keychain dump (§2)
│   │   ├── Filesystem inspection → check all data storage (§7)
│   │   ├── Runtime hooks → Frida/Objection (§5)
│   │   └── Binary analysis → class-dump decrypted binary (§6)
│   └── No → limited testing
│       ├── Re-sign with Frida gadget for runtime access
│       ├── Backup extraction for data analysis
│       └── Network-level testing (proxy + SSL bypass)
│
├── SSL pinning blocking proxy?
│   └── Yes → see mobile-ssl-pinning-bypass SKILL.md
│
├── URL schemes registered?
│   ├── OAuth callback via URL scheme? → hijacking risk (§3.2)
│   ├── Universal Links configured? → check AASA (§4.1)
│   └── Scheme used for sensitive actions? → test interception
│
├── Binary protections adequate?
│   ├── Missing PIE? → ASLR disabled (§6.1)
│   ├── No stack canaries? → overflow risk (§6.1)
│   └── Still encrypted? → decrypt first (§6.2)
│
├── Data storage secure?
│   ├── Tokens in NSUserDefaults? → plaintext extraction (§7.1)
│   ├── Keychain protection class? → AfterFirstUnlock = risky (§2.1)
│   ├── Screenshots captured? → check Snapshots dir (§7.1)
│   └── Keyboard cache? → check for sensitive autocomplete (§7.1)
│
├── ATS configured?
│   ├── ArbitraryLoads = true? → HTTP downgrade possible (§8)
│   └── Domain exceptions? → targeted HTTP interception
│
└── Runtime manipulation needed?
    ├── Jailbreak detection blocking? → ios jailbreak disable (§5.2)
    ├── Need to bypass auth check? → hook + modify return (§5.1)
    └── Need to trace API calls? → method hooking (§5.2)