Module 0 — Legal, Ethics, Scope & Lab Setup

• 0.1 Authorization & rules of engagement (RoE)
  • Written authorization checklist
  • Scope definition: in-scope assets, out-of-scope limits
  • Data handling, privacy, chain of custody
  • Emergency contacts & escalation
• 0.2 Test types and methodologies
  • Black-box, gray-box, white-box testing distinctions
  • Risk-based vs feature-based assessments
  • Goal setting: confidentiality, integrity, availability objectives
• 0.3 Lab & safe environment setup (recommended)
  • Hardware options: physical iPhones/iPads (jailbroken & non-jailbroken), macOS host
  • Emulators/simulators: differences (iOS Simulator vs real device)
  • Network lab: isolated VLAN, proxying, MITM lab machines
  • Recommended VM images, snapshots, and backups
• 0.4 Evidence collection & reporting best practices
  • Triage forms, screenshots, logs, PCAPs, timestamps, reproducibility
  • Report templates, severity mapping, CVSS basics
  • Disclosure workflow & remediation verification

Module 1 — iOS Basics & App Anatomy

• 1.1 iOS architecture & app lifecycle (high level)
  • Process model, sandboxing, entitlements, provisioning
  • App bundle structure: .app folder, Info.plist, assets
• 1.2 IPA, provisioning profiles, and code signing
  • IPA format, payload layout, embedded provisioning profile
  • Code signing basics and entitlements (conceptual)
• 1.3 Mach-O binary format & Objective-C/Swift runtime fundamentals
  • Symbols, sections, Objective-C runtime (classes, selectors), Swift metadata
• 1.4 iOS storage primitives
  • NSUserDefaults/UserDefaults, SQLite, Realm, Keychain basics
• 1.5 Networking stack overview
  • NSURLSession, CFNetwork, TLS basics, certificate pinning concept
• 1.6 App protections & common countermeasures (overview)
  • Obfuscation, anti-tamper, anti-debug, jailbreak/root detection, runtime integrity checks, SSL pinning

Module 2 — Reconnaissance & Information Gathering

• 2.1 Passive recon from App Store / TestFlight / APK mirrors
  • Metadata, permissions, release notes, binaries (how to obtain IPAs legally)
• 2.2 Static metadata collection
  • Info.plist, entitlements, URL schemes, deep links, supported architectures
• 2.3 OSINT & infrastructure mapping
  • Backend domains, API endpoints, certificate info, mobile API discovery
• 2.4 Binary acquisition (legal & safe methods)
  • Downloading IPAs from TestFlight/App Store (authorized flows), enterprise builds
• 2.5 Initial threat modeling for the app
  • Assets, trust boundaries, attacker capabilities & likely attack vectors

Module 3 — Static Analysis (conceptual → tooling)

• 3.1 Manual inspection of bundle contents
  • Info.plist, embedded.mobileprovision, resource files, configuration leaks
• 3.2 Class-dump & header reconstruction (conceptual)
  • Recreating class interfaces and method lists
• 3.3 Decompilation & disassembly overview
  • Hopper, Ghidra, IDA, Binary Ninja — what each gives you conceptually
• 3.4 Swift reverse engineering basics (metadata, mangled names)
• 3.5 Searching for secrets & misconfigurations
  • Hardcoded keys, embedded credentials, API keys, dev endpoints
• 3.6 Static analysis tools & scanners (list + purpose)
  • mobSF (Mobile Security Framework), iOS-specific linters, strings, grep, floss

Module 4 — Dynamic Analysis & Instrumentation (non-exploitative)

• 4.1 Runtime observation techniques
  • Logging, network inspection, local storage observation
• 4.2 Proxying & MITM (conceptual)
  • Burp/mitmproxy usage with mobile: device proxying, certificate installation, TLS limits
• 4.3 Debugging basics on iOS
  • lldb overview, process attachment concepts, sandbox constraints
• 4.4 Tainting & data flow observation (conceptual)
  • Tracing sensitive data from source (input) to sink (network, file)
• 4.5 App behavioral profiling
  • Monitoring app lifecycle and network patterns

Module 5 — Runtime Hooking & Frida (conceptual + safe guidance)

• 5.1 What is Frida and when to use it
  • Frida architecture (agent + host), dynamic instrumentation benefits
• 5.2 Frida session lifecycle & primitives (conceptual)
  • Interceptors, Stalker, NativeFunction, Memory.read/write (concepts)
• 5.3 Typical Frida use-cases (authorized testing)
  • Inspecting method calls, bypassing client-side logic for testing, extracting runtime secrets
• 5.4 Anti-Frida & anti-instrumentation concepts
  • Detecting injected agents, checksums, dynamic integrity checks
• 5.5 Safe, high-level examples of hooks (no copy/paste exploit code)
  • How to approach hooking: identify target functions, log inputs/outputs, validate effects
• 5.6 Tooling ecosystem: Objection, frida-swift, frida-objc, gadget injection options (conceptual)

Module 6 — Jailbreak Detection, Anti-Debug & Anti-Tamper

• 6.1 Typical jailbreak checks & detection vectors
  • File path checks, process checks, URL scheme checks, sandbox escapes (conceptual)
• 6.2 Anti-debug / anti-attach techniques apps use
  • ptrace, sysctl checks, signal handlers (conceptual)
• 6.3 Counter-anti-debug and bypassing approaches (conceptual)
  • Hardening vs testing: safe ways to test anti-debug without posting weaponized steps
• 6.4 Tamper detection & runtime integrity checks
  • Checksums, encrypted resources, runtime attestation concepts
• 6.5 Best practices for responsibly testing and reporting bypassable protections

Module 7 — SSL / TLS and Certificate Pinning (analysis + testing)

• 7.1 TLS basics & failure modes
• 7.2 Pinning approaches (public key, certificate, SPKI) and how apps implement them (conceptual)
• 7.3 Testing strategies to verify pinning and check fallback behaviors
• 7.4 MitM evasion defenses and responsible testing notes
• 7.5 Defensive remediation guidance for developers

Module 8 — Authentication & Session Management Attacks

• 8.1 Local authentication flows (PIN, biometric, server verification)
• 8.2 Session token lifecycle, renewal, revocation, and fixation issues
• 8.3 Broken authentication scenarios and tests
  • Weak session tokens, predictable tokens, insufficient logout, duplicate login handling
• 8.4 OAuth / SSO integration pitfalls
• 8.5 Recommended tests and safe verification steps

Module 9 — Data Storage & Keychain Attacks

• 9.1 iOS Keychain model & access groups (conceptual)
• 9.2 Common misuses of secure storage
• 9.3 Local file storage weaknesses (unencrypted DBs, caches, logs)
• 9.4 Safe methods to verify sensitive data leakage (without providing exploit scripts)
• 9.5 Mitigations and secure storage best practices

Module 10 — Reverse Engineering, Binary Patching & Repackaging (overview + ethics)

• 10.1 When and why to patch or repackage an app in testing
• 10.2 High-level process: unpack → analyze → modify → repackage → re-sign (conceptual)
• 10.3 Code signing, entitlements, provisioning constraints (conceptual)
• 10.4 Common pitfalls and safe lab practices (don’t present weaponized steps)
• 10.5 Secure reporting: how to present proof of concept without shipping exploit code

Module 11 — Advanced Code & Flow Analysis

• 11.1 Dynamic taint analysis & data flow tracing concepts
• 11.2 Finding logic flaws: authorization, business logic, race conditions
• 11.3 Interplay of client & server logic — how to model and test
• 11.4 Advanced reverse engineering topics (Swift generics, runtime symbols)

Module 12 — Exploit Development (conceptual, lab-only)

• 12.1 Memory corruption basics (conceptual only)
• 12.2 Exploit mitigations on iOS (ASLR, DEP, code signing) — why real exploits are hard
• 12.3 Vulnerability chaining and the ethics of exploitation
• 12.4 Safe, simulated exploit examples for learning inside isolated lab VMs (recommendations — no weaponized code here)

Module 13 — Runtime Patching & Function Hooking Techniques (advanced, conceptual)

• 13.1 Inline patching vs trampolines — concepts
• 13.2 Using runtime hooks to change business logic (authorized testing)
• 13.3 Detecting and defeating self-integrity checks (conceptual)
• 13.4 Best practices for building PoCs that are safe, reproducible, and non-destructive

Module 14 — Obfuscation & Protections: How They Work and How to Assess Them

• 14.1 Types of obfuscation: symbol/identifier, control-flow, string encryption
• 14.2 Packing & runtime loaders
• 14.3 Measuring protection strength and limitations
• 14.4 Guidance for developers: choosing protections that don’t break maintainability

Module 15 — Mobile Backend Attacks & API Security

• 15.1 API enumeration and attack surface mapping
• 15.2 Common API flaws: broken access control, IDOR, excessive data exposure
• 15.3 Rate limiting, throttling, and brute force protections
• 15.4 Testing methodology and responsible disclosure steps to backend teams

Module 16 — Advanced Topics: Side-channels, Inter-process, and System-level Issues

• 16.1 Side-channel information leakage (timing, resource usage)
• 16.2 Inter-app communication risks (URL schemes, pasteboard, XPC)
• 16.3 Exploiting misconfigured entitlements & app groups (conceptual)
• 16.4 Hardware-assisted protections and bypass realities

Module 17 — Automation, Tooling & Frameworks

• 17.1 Scripting reconnaissance and repeated checks (conceptual)
• 17.2 CI/CD security checks for mobile apps
• 17.3 Useful toolchain: mobSF, Frida, Objection, class-dump, radare2, Hopper, Ghidra, IDA, Burp, mitmproxy, lldb, Xcode tools, codesigners
• 17.4 Building reproducible testcases & PoCs safely

Module 18 — Reporting, Remediation, and Developer Collaboration

• 18.1 Structuring a technical pentest report (Executive Summary → Technical → PoC → Remediation)
• 18.2 Risk rating, CVSS and practical business impact
• 18.3 Recommended fixes for frequent issues
• 18.4 Retest and verification process

Module 19 — Defensive Guidance & Secure Development Lifecycle (SDLC)

• 19.1 Secure coding patterns for iOS apps
• 19.2 Threat modeling during design
• 19.3 Secure third-party library management
• 19.4 Runtime monitoring and detection as defense

Module 20 — Appendix: Reference Material, Cheat Sheets, and Labs

• 20.1 Recommended reading & blogs, vulnerability databases, CVE feeds
• 20.2 Labs, CTFs and learning resources (safe environments)
• 20.3 Glossary of iOS pentest terms
• 20.4 Example RoE template, test checklists, report templates

For each module I will include (per your request)

• Purpose & learning objectives
• Prerequisites
• Full tool list with alternatives (why choose each)
• Step-by-step methodology at the conceptual level
• Safe, reproducible lab exercises (where applicable) using isolated devices/VMs
• What to capture as evidence and how to present it
• Common pitfalls, mitigations, and developer recommendations
• Links to further reading & reference (where publicly available)