iOS Mobile Application Penetration Testing

Thin router for an iOS app security assessment. Full OWASP MASTG coverage (recon → static → dynamic → network → storage → crypto → auth → reporting). Detailed runbooks live under workflows/ and methodology/; load them only when needed.

When to Use

• New iOS application security assessment (IPA + installed app).
• Bypass SSL pinning, jailbreak detection, biometric, anti-debug.
• Extract and triage keychain / NSUserDefaults / files / SQLite.
• Intercept and tamper HTTPS / gRPC / WebSocket traffic.
• OWASP MASTG / MASVS compliance testing.
• Analyze a decrypted or encrypted Mach-O binary.

Trigger Phrases

"pentest iOS app", "test this IPA", "bypass SSL pinning iPhone", "extract keychain", "MASTG iOS", "iOS jailbreak bypass", "analyze .ipa", "test iPhone app".

When NOT to Use This Skill

• Android APK analysis → use android-pentest.
• Generic web API testing for the backend → use web-pentest / api-pentest.
• iOS source-code review (you have the repo) → use secure-code-review with iOS language packs.
• macOS desktop app analysis → use macos-pentest.

Decision Tree

target acquired?
├── no binary yet → workflows/ipa_decryption.md
└── yes
    ├── need HTTPS visibility? → workflows/ssl_pinning_bypass.md
    ├── app exits on jailbroken device? → workflows/jailbreak_detection_bypass.md
    ├── hunting credentials/tokens? → workflows/keychain_extraction.md
    ├── testing login / biometric? → workflows/auth_testing.md
    └── full engagement → workflows/complete_assessment.md

Parallelism Hints

Run concurrently (independent I/O, no shared state):

• class-dump -H App.app/App -o headers/
• otool -L App.app/App and otool -hv App.app/App
• strings -a App.app/App | grep ...
• plutil -p App.app/Info.plist
• Objection enumeration in a separate spawn.

Must run sequentially (shared Frida session / spawn state):

• Frida --no-pause spawn → wait for bypass script to land → drive app → then attach further scripts.
• Objection ios sslpinning disable → then any traffic-dependent command.
• ideviceimagemounter → then frida-ps -U.
• Keychain dump requires app launched at least once post-install.

Sub-Agent Delegation

Spawn a sub-agent when you can crisply isolate a scope:

• Static-binary sub-agent — give it the decrypted App.app/, it runs class-dump + otool + strings + framework inventory in parallel, returns a structured summary of classes of interest, hardcoded secrets, and insecure API usage.
• Keychain-extraction sub-agent — give it <bundle_id>, it runs objection ... keychain dump --json, classifies each entry by accessibility/ACL, emits findings per schemas/finding.json.
• Optional: network-capture sub-agent driving Burp via proxy API while the main agent drives the UI.

Do not split Frida spawn + instrumentation across sub-agents — the Frida session is stateful and tied to one process.

Reasoning Budget

Use extended thinking for:

• Interpreting decompiled Objective-C / Swift (Hopper / Ghidra / IDA output).
• Designing custom Frida hooks when universal bypass fails.
• Reasoning about cryptographic flow (key origin → cipher → storage).
• MASVS severity triage when multiple subtle issues compound.

Skip extended thinking for:

• Running canned Frida / Objection scripts from scripts/.
• Parsing ios keychain dump --json output (pattern match).
• otool / class-dump invocation and output collection.
• File downloads, device enumeration, SSH pulls.

Multimodal Hooks

Mobile MCP (@anthropic/mobile-mcp --ios) provides iOS simulator / device UI automation:

• Jailbreak-detection modal — screenshot the warning pre-bypass, then post-bypass absence, as evidence.screenshot.
• Biometric prompt — capture Face ID / Touch ID sheet to prove the gate exists, then confirm bypass entered the protected screen.
• App-switcher snapshot leak — screenshot the snapshot cache entry showing sensitive data on backgrounding.
• WebView auth flow — capture the login redirect chain visually for SSO findings.

~/.claude/mcp.json:

{"mcpServers": {"mobile-mcp": {"command": "npx", "args": ["-y", "@anthropic/mobile-mcp", "--ios"]}}}

Structured Output

Emit every finding as JSON conforming to schemas/finding.json. iOS-specific fields: affected.bundle_id, affected.ios_version, affected.device_udid, affected.jailbroken, mastg_id, evidence.frida_pid, evidence.keychain_dump, evidence.screenshot.

Workflow Index

Workflow	File
Full assessment runbook	workflows/complete_assessment.md
SSL pinning bypass	workflows/ssl_pinning_bypass.md
Jailbreak-detection bypass	workflows/jailbreak_detection_bypass.md
Keychain extraction & triage	workflows/keychain_extraction.md
IPA decryption / acquisition	workflows/ipa_decryption.md
Auth & biometric testing	workflows/auth_testing.md

Methodology Index

Area	File
Recon	methodology/recon.md
Static analysis	methodology/static_analysis.md
Dynamic analysis	methodology/dynamic_analysis.md
Network testing	methodology/network_testing.md
Data storage	methodology/data_storage.md
Crypto testing	methodology/crypto_testing.md
Auth testing	methodology/auth_testing.md

Payloads Index

File	Purpose
payloads/jailbreak_detection_paths.txt	Common files/schemes iOS apps probe for jailbreak
payloads/url_scheme_tests.txt	URL scheme / deep-link test vectors

Frida Script Index (scripts/)

Script	Purpose
ssl_pinning_bypass.js	Universal SSL/TLS pinning bypass
jailbreak_bypass.js	Jailbreak detection bypass
biometric_bypass.js	Touch ID / Face ID bypass
keychain_hooks.js	Keychain operation monitoring
crypto_hooks.js	Cryptographic operation tracing
method_tracer.js	Generic Objective-C method tracer

References Index

File	Purpose
references/ios_vulns.md	iOS vuln classes, severity tables, MASVS map
references/troubleshooting.md	Frida / pinning / proxy issue triage
references/frida_ios_snippets.md	Reusable Frida code snippets
references/bounty_patterns_2024_2026.md	Post-2023 bounty TTPs (URL-scheme / Universal-Link hijack, WebView deep-link XSS, Keychain IAM-token insecurity)
checklists/owasp_mastg_ios.md	Full MASTG iOS checklist
templates/finding_report.md	Markdown finding template

Examples

File	Purpose
examples/initial_setup.md	First-contact blueprint
examples/ssl_bypass_run.md	Pinning-bypass blueprint
examples/keychain_dump.md	Keychain dump & triage blueprint

Tools

Tool	Purpose	Install
Frida / frida-tools	Dynamic instrumentation	pip install frida-tools (≥ 16.6)
Objection	Mobile exploration REPL	pip install objection (≥ 1.11)
libimobiledevice	Device communication	brew install libimobiledevice
ios-deploy	App deploy	brew install ios-deploy
ideviceinstaller	App install / list	brew install ideviceinstaller
class-dump	ObjC header extraction	brew install class-dump
frida-ios-dump	FairPlay decryption	github.com/AloneMonkey/frida-ios-dump
Burp Suite	HTTPS interception	PortSwigger
Hopper / IDA / Ghidra	Binary RE	Vendor / GitHub
Mobile MCP	UI automation + screen capture	npx @anthropic/mobile-mcp --ios

Prerequisites Quickcheck

Run before every engagement — fail fast if the lab is broken.

idevice_id -l               # at least one UDID listed
ideviceinfo | grep ProductVersion
frida-ps -U                 # frida-server reachable
objection -g <bundle_id> explore --startup-command 'ios info binary; exit'

Jailbroken setup: OpenSSH + Frida (Sileo repo build.frida.re) + AppSync Unified + Filza. Non-jailbroken fallback: patch IPA with objection patchipa to inject Frida Gadget, or mount the developer disk image with ideviceimagemounter.

Last Validated

2026-04. Frida ≥ 16.6, Objection ≥ 1.11, iOS 15–17 targets. For iOS 18+ jailbreak options shift to userspace-only (Dopamine/palera1n rootless) — SSH path is /var/jb/usr/bin/ssh and Frida server lives at /var/jb/usr/sbin/frida-server.