SKILL: macOS Security Bypass — Expert Attack Playbook

AI LOAD INSTRUCTION: Expert macOS security bypass techniques. Covers TCC bypass, Gatekeeper evasion, SIP restrictions, sandbox escape, and entitlement abuse. Base models miss version-specific bypass nuances and protection interaction effects.

0. RELATED ROUTING

Before going deep, consider loading:

• macos-process-injection when you need dylib injection, XPC exploitation, or Electron abuse after achieving initial access
• linux-privilege-escalation for Unix-layer privesc techniques that also apply to macOS (SUID, cron, writable paths)
• linux-security-bypass for shared Unix security bypass concepts

Advanced Reference

Also load TCC_BYPASS_MATRIX.md when you need:

• Per-macOS-version TCC bypass mapping
• Protection-type-specific techniques (Camera, Microphone, FDA, Automation)
• MDM/configuration profile abuse patterns

1. TCC (TRANSPARENCY, CONSENT, CONTROL) OVERVIEW

TCC is macOS's permission framework controlling access to sensitive resources (camera, microphone, contacts, full disk access, etc.).

1.1 TCC Database Locations

-- Query TCC database (requires FDA or SIP off)
sqlite3 ~/Library/Application\ Support/com.apple.TCC/TCC.db \
  "SELECT service, client, allowed FROM access;"

1.2 TCC Bypass Categories

1.3 Known TCC Bypass Patterns

Terminal / iTerm FDA inheritance: Terminal.app granted FDA → any command run inherits FDA → read any file.

# If Terminal has FDA, this reads protected files directly
cat ~/Library/Mail/V*/MailData/Envelope\ Index
cat ~/Library/Messages/chat.db

Finder automation: Automate Finder (lower permission bar) to access files in protected locations.

tell application "Finder"
  set f to POSIX file "/Users/target/Library/Mail/V9/MailData/Envelope Index"
  duplicate f to desktop
end tell

System Preferences / System Settings injection: Inject into a process that already has TCC permissions by writing to its Application Scripts folder.

MDM profile abuse: PPPC profiles can pre-approve TCC permissions. Rogue MDM enrollment or compromised MDM server → push PPPC payload.

2. GATEKEEPER BYPASS

Gatekeeper blocks unsigned or unnotarized apps from executing. Core enforcement depends on the com.apple.quarantine extended attribute.

2.1 Quarantine Attribute Removal

# Check quarantine attribute
xattr -l /path/to/app
# Output: com.apple.quarantine: 0083;...

# Remove quarantine (requires write access)
xattr -d com.apple.quarantine /path/to/app
# Recursive for app bundles
xattr -rd com.apple.quarantine /path/to/MyApp.app

2.2 Bypass Techniques

2.3 Gatekeeper Check Flow

App launched
│
├── com.apple.quarantine attribute present?
│   ├── No → execute (no Gatekeeper check)
│   └── Yes ↓
│
├── Code signature valid?
│   ├── No → block
│   └── Yes ↓
│
├── Notarized (stapled ticket or online check)?
│   ├── No → block (Catalina+)
│   └── Yes → execute
│
└── User override? (right-click → Open → confirm)
    └── Bypasses Gatekeeper once for this app

3. SIP (SYSTEM INTEGRITY PROTECTION)

SIP restricts root from modifying protected system locations, loading unsigned kernel extensions, and debugging system processes.

3.1 SIP-Protected Locations

/System/
/usr/ (except /usr/local/)
/bin/
/sbin/
/var/ (selected subdirs)
/Applications/ (pre-installed Apple apps)

3.2 SIP Status & Configuration

csrutil status              # Check SIP status
csrutil disable             # Recovery Mode only
csrutil enable --without fs # Partial disable (risky)

3.3 Entitlements That Bypass SIP

3.4 Historical SIP Bypasses

4. SANDBOX ESCAPE

macOS sandboxing (App Sandbox, via sandbox-exec or entitlements) restricts app access to filesystem, network, and IPC.

4.1 Office Sandbox Escape Patterns

4.2 IPC-Based Escape

4.3 Browser Sandbox

• Chromium: Multi-process model, renderer is sandboxed, browser process is not
• Safari: WebContent process sandboxed, parent Safari process has more privileges
• Exploit chain: renderer RCE → sandbox escape (via IPC bug to browser process) → system access

5. CODE SIGNING & ENTITLEMENTS

5.1 Inspecting Signatures and Entitlements

codesign -dv --verbose=4 /path/to/app       # Signature details
codesign -d --entitlements :- /path/to/app   # Dump entitlements
security cms -D -i /path/to/mobileprovision  # Provisioning profile

# Verify signature validity
codesign --verify --deep --strict /path/to/app
spctl --assess --type execute /path/to/app   # Gatekeeper assessment

5.2 Entitlement Abuse for Privilege Escalation

5.3 Hardened Runtime Bypass

Hardened Runtime prevents: DYLD env vars, debugging, unsigned memory execution. Bypasses:

• Find entitled apps that weaken Hardened Runtime (disable-library-validation)
• Exploit JIT-entitled apps (browsers, VMs) for unsigned code execution
• Use get-task-allow entitled debug builds left in production

5.4 Library Validation Bypass

Library validation ensures only Apple-signed or same-team-signed dylibs load.

# Find apps with library validation disabled
codesign -d --entitlements :- /Applications/*.app/Contents/MacOS/* 2>/dev/null | \
  grep -l "disable-library-validation"

6. PERSISTENCE AFTER BYPASS

7. macOS SECURITY BYPASS DECISION TREE

Target is macOS endpoint
│
├── Need to execute untrusted binary?
│   ├── Quarantine attribute present?
│   │   ├── Yes → xattr -d com.apple.quarantine (§2.1)
│   │   └── No → execute directly
│   └── Gatekeeper still blocks?
│       ├── Signed but not notarized → right-click → Open override
│       └── Unsigned → embed in signed bundle or use archive tricks (§2.2)
│
├── Need access to TCC-protected resources?
│   ├── FDA-granted app available?
│   │   ├── Yes → exploit FDA app context (§1.3)
│   │   └── No ↓
│   ├── Automation permission obtainable?
│   │   ├── Yes → Apple Events to TCC-granted app (§1.3)
│   │   └── No ↓
│   ├── SIP disabled?
│   │   ├── Yes → direct TCC.db modification (§1.2)
│   │   └── No → check version-specific TCC bypass (→ TCC_BYPASS_MATRIX.md)
│   └── MDM present?
│       └── Compromised MDM → push PPPC profile (§1.3)
│
├── Need to bypass SIP?
│   ├── Check macOS version → historical SIP CVE? (§3.4)
│   ├── Find entitled Apple binary → piggyback SIP-bypass entitlement (§3.3)
│   └── Recovery Mode access? → csrutil disable (§3.2)
│
├── Need sandbox escape?
│   ├── Office macro context → dialog/LaunchAgent tricks (§4.1)
│   ├── XPC service with weak validation → IPC escape (§4.2)
│   └── Browser context → renderer → sandbox escape chain (§4.3)
│
├── Need to inject into signed process?
│   ├── disable-library-validation entitlement? → dylib injection
│   ├── allow-dyld-environment-variables? → DYLD_INSERT_LIBRARIES
│   ├── get-task-allow? → debugger attach
│   └── None → check macos-process-injection SKILL.md
│
└── Need persistence?
    └── Choose method by access level (§6)

8. QUICK REFERENCE: TOOL COMMANDS

# Enumerate TCC permissions
tccutil reset All                              # Reset all TCC (admin)
sqlite3 TCC.db "SELECT * FROM access;"         # Read TCC DB

# Gatekeeper status
spctl --status                                 # Gatekeeper enabled?
spctl --assess -v /path/to/app                 # Check app assessment

# SIP status
csrutil status

# Find interesting entitlements across system
find /System/Applications /Applications -name "*.app" -exec sh -c \
  'codesign -d --entitlements :- "$1" 2>/dev/null | grep -q "disable-library-validation" && echo "$1"' _ {} \;

# List loaded kexts (kernel extensions)
kextstat | grep -v com.apple

# Sandbox profile inspection
sandbox-exec -p "(version 1)(allow default)" /bin/ls  # Test sandbox rules