macos-security

name	macos-security
description	macOS red team and security assessment — SIP/TCC bypass, Endpoint Security framework, Apple Silicon/T2/M-series attacks, Mach-O analysis, Keychain extraction, MDM bypass, LaunchAgents/Daemons persistence, and macOS-native malware analysis.
origin	github-trending-2026
version	0.2.0.2
compatibility	Claude Code, Agent SDK
allowed-tools	Bash, Read, Edit, Write, Glob, Grep
metadata	{"domain":"macos","category":"macos","tool_count":13,"guide_count":2,"mitre":"TA0005-Defense Evasion, T1547-Boot or Logon Autostart, T1555-Credentials from Password Stores","keywords":["macos","sip","tcc","endpoint-security","mach-o","keychain","apple-silicon","m2","launchd","mdm","knockknock","lulu"],"last_reviewed":"2026-07-26"}

Skill: macOS Security Assessment

Supplementary Files:

• payloads.md — Command catalogue for macOS red team and malware analysis: 18 sections covering recon, SIP/TCC bypass, ESF event logging, LaunchAgents/Daemons persistence, Keychain extraction, Cookies.binarycookies, Apple Silicon (arm64e, PAC, sealed snapshots), MDM profile analysis, Mach-O analysis (otool, jtool2, machOView), code signing/notarization, process/memory analysis, network analysis, persistence enumeration, defense bypass (AMFI, sandbox), Objective-See tools (KnockKnock, LuLu, BlockBlock, OverSight), and a cheat sheet. 60+ code blocks with real macOS CLI syntax.
• test-cases.md — Structured test cases (TC-MO-001..018): system profiling, SIP status check, TCC.db audit, LaunchAgents/Daemons enumeration, Keychain extraction via security, Cookies.binarycookies parsing, MDM profile analysis, Mach-O analysis, code signing verification, KnockKnock persistence scan, ESF event logging, Apple Silicon PAC check, plus Apple Silicon boot chain, ESF client construction, TCC.db deep reverse engineering, MDM profile abuse, unified log hunting, AMSI/AMFI bypass, and Keychain offline cracking. Includes a Verification Checklist.
• guides/macos-security-playbook.md — End-to-end operational playbook: macOS security architecture (SIP/TCC/AMFI/sandbox/ESF/Secure Boot), Apple Silicon specifics (arm64e, PAC, Rosetta 2, sealed system snapshots), building a macOS test lab, red team methodology, real-world macOS threats (XCSpy, Shlayer, Bundlore, Silver Sparrow, NodeStealer), defense patterns, and references.
• guides/macos-security-deep-dive.md — Deep-dive on Apple Silicon (M1/M2/M3/M4) security architecture: boot chain (SSV/Rosetta/kernel), PPL (Page Protection Layer), pointer authentication codes, kext vs System Extensions, the Endpoint Security Framework API surface, TCC.db reverse engineering methodology, recent CVEs (CVE-2023-32434/32435/41990), and the macOS red team tradecraft playbook.

Summary

macOS security assessment skill covering Apple's desktop/laptop platform from a red team and malware analyst perspective. This skill addresses the modern macOS attack surface: System Integrity Protection (SIP/rootless), Transparency Consent and Control (TCC), Endpoint Security framework (ESF), Apple Silicon (M1/M2/M3/M4 with arm64e and Pointer Authentication Codes), T2 chip on Intel Macs, code signing + notarization enforcement, LaunchAgents/LaunchDaemons persistence, Keychain credential stores, MDM profile abuse, and Mach-O binary analysis.

Tools: Objective-See suite (KnockKnock, LuLu, BlockBlock, OverSight, TaskExplorer, What's Your Sign?), sindresorhus/Equity, mSCP (macOS Security Compliance Project), machOView, Hopper Disassembler, Ghidra (Mach-O plugin), jtool2, ldid, plus native CLI (system_profiler, csrutil, tccutil, security, codesign, otool, nm, vmmap, lldb, profiles, airport).

Domain: macos

MITRE ATT&CK: T1547-Boot or Logon Autostart (LaunchAgents/Daemons, login items), T1555-Credentials from Password Stores (Keychain, Cookies.binarycookies), T1059-Command and Scripting Interpreter (zsh, osascript), T1068-Exploitation for Privilege Escalation (SIP bypass, SUID abuse), T1106-Native API (Mach APIs, launchd), T1620-Reflective Code Loading (DYLD injection), TA0005-Defense Evasion (AMFI bypass, notarization abuse, TCC bypass).

Description

macOS is no longer a niche enterprise endpoint. As of 2026 it commands roughly a quarter of the U.S. enterprise laptop market, is the default developer machine at most Fortune 500 technology companies, and is increasingly the executive laptop of choice. It is also a strange target: it runs a Darwin/BSD core (so it has UNIX permissions, file flags, chroot, seatbelt sandbox profiles), but it is wrapped in a sophisticated proprietary security architecture (System Integrity Protection, Apple Mobile File Integrity / AMFI, TCC privacy consent, Secure Boot, sealed system snapshots on Apple Silicon, and the Endpoint Security framework). Most offensive techniques ported from Linux work, but the interesting bugs and persistence mechanisms are macOS-specific — and the defenders have a 10-year head start via Patrick Wardle's research, the Objective-See tooling, Apple's Platform Security Guide, and the macOS Security Compliance Project (mSCP).

This skill is the macOS counterpart to av-edr-evasion (which focuses on Windows Defender / commercial EDR) and binary-reverse (which is platform-agnostic but mostly ELF/PE-flavored). Where those skills cover Windows and Linux, this skill covers the macOS-specific attack surface: csrutil/nvram for SIP, tccutil + TCC.db for privacy, security CLI for Keychain, codesign/spctl for signing and notarization, otool -L and jtool2 for Mach-O introspection, profiles for MDM, and the EndpointSecurity framework for the same event stream that commercial EDR (Falcon, SentinelOne, Jamf Protect, Microsoft Defender for Endpoint) subscribes to.

Eight things distinguish macOS attacks from generic UNIX attacks:

1. SIP (System Integrity Protection) is the new root — On 2015+ macOS, even root cannot write to /System, /usr, /bin, /sbin, certain protected subdirs of /Library, or the TCC database by default. Processes that try must be Apple-signed with the right entitlements, or SIP itself must be disabled (recovery-mode csrutil disable). Modern macOS attacks either work within SIP (persistence in user-writable locations, TCC.db manipulation under granted entitlements) or seek SIP bypasses (CVE-2019-8805, CVE-2020-3837, CVE-2023-32434 — the latter a memory corruption in the boot ROM image parser, unpatchable by software on Apple Silicon).

2. TCC (Transparency, Consent, and Control) is the new permission gate — Every macOS app that wants to read user data (location, camera, microphone, contacts, calendars, reminders, photos, Mail, Safari history, Messages, full disk access, accessibility control, automation) must request consent at first use, recorded in /Library/Application Support/com.apple.TCC/TCC.db (system) and ~/Library/Application Support/com.apple.TCC/TCC.db (user). TCC bypass is the macOS analog of a Windows UAC bypass — historically via DYLD insertion into a TCC-entitled binary (Xcode.app, swift), via env-var abuse, or via direct SQLite manipulation when SIP is weakened.

3. The Endpoint Security framework (ESF) is the EDR's eyes — and yours — Introduced in macOS 10.15 Catalina (2019) and hardened repeatedly since, ESF is the only supported API for monitoring process exec, file writes, endpoint disk I/O, mount/unmount, opendirectory lookups, and (on Monterey+) login/logout. Commercial EDR (CrowdStrike, SentinelOne, Defender for Endpoint, Jamf Protect) is required by Apple to subscribe to ESF — and a red team operator who can run eslogger or build their own ESF client gets the same telemetry, for free, on any Mac they have admin on.

4. Apple Silicon changes the rules — PAC, sealed snapshots, Rosetta 2 — On M-series Macs, the kernel runs arm64e with Pointer Authentication Codes (PAC) on every function pointer and return address — most classic ROP/JOP chains fail. The system volume is a cryptographically sealed APFS snapshot (/System/Volumes/Data is mutable, ///System are read-only and hash-checked at every boot). Kernel extensions are effectively dead for third parties; the only supported path is System Extensions (user-land) and DriverKit. Rosetta 2 (x86_64 emulation) is an entire second ABI with its own historical bugs (CVE-2021-30717 — Rosetta translation bypass of code signing checks). Apple Silicon also brought (2021), the first malware family observed shipping an arm64 payload alongside x86_64.

Difference from mobile-security: mobile-security is iOS/Android — app review bypass, certificate pinning, APK/IPA reverse engineering, mobile data protection at the application layer. THIS skill is macOS desktop/laptop specifically — SIP/TCC/ESF, LaunchAgents/Daemons persistence, Mach-O (not ELF/PE), Keychain (not Android Keystore), MDM profile analysis as an enterprise control plane. The platforms share a kernel (Darwin) and code signing (codesign + ldid) but the attack surfaces are otherwise distinct. iOS additionally has its own sandbox and entitlement system that differs in detail.

Difference from av-edr-evasion: av-edr-evasion covers Windows Defender, commercial EDR (CrowdStrike, SentinelOne, Defender for Endpoint), and bypass techniques for those. THIS skill covers the macOS-specific defense stack: AMFI, Gatekeeper, XProtect, MRT (Malware Removal Tool), TCC, and the macOS-native EDR surface (System Extensions, ESF). Where av-edr-evasion might cover direct syscalls and process doppelgänging on Windows, this skill covers signed-and-notarized droppers, TCC bypass via entitlement inheritance, and persistence in LaunchAgents.

Difference from binary-reverse: binary-reverse covers static/dynamic analysis broadly — PE, ELF, and Mach-O. THIS skill narrows to Mach-O specifically: otool, nm, jtool2, machOView, Ghidra Mach-O plugin, disassembling arm64/arm64e with PAC-aware tooling, dumping entitlements, walking the load commands. The Mach-O format, the Objective-C runtime metadata, and the Swift symbol mangling are macOS-specific.

Difference from digital-forensics: digital-forensics covers IR artifacts broadly (logs, file system timeline, memory). THIS skill covers macOS-specific forensic artifacts: the unified log (log show), FSEvents, Spotlight metadata, TCC.db audit, Keychain access history, Spotlight importers, and the securenotes table in the user keychain. Where digital-forensics might describe Windows event log analysis, this skill covers log show --predicate 'subsystem == "com.apple.securityd"'.

Difference from container-security and cloud-security: those cover Linux containers and cloud IaaS. macOS has its own containerization model (per-app sandbox via sandboxd, hardened runtime via entitlements, App Sandbox container directories at ~/Library/Containers/<bundle-id>/). The macOS container model is per-process and enforced by the kernel, not by a container runtime.

Use Cases

• SIP/TCC bypass for red team: Identify the running SIP configuration (csrutil status), enumerate the TCC-protected resources the foothold user can access, look for entitlement-rich binaries (Xcode, Mail, Safari) that can be used as proxies via DYLD insertion or osascript automation, and document paths to bypass TCC where present.
• Keychain, cookies, and Safari data extraction: Once on a Mac with the user logged in, dump ~/Library/Keychains/login.keychain-db via the security CLI, extract Safari cookies from Cookies.binarycookies, parse Safari history from History.db, and recover saved Wi-Fi PSKs via security find-generic-password.
• MDM profile analysis and abuse: Enumerate installed configuration profiles (profiles list -output user), reverse-engineer the payload of each profile to find enterprise restrictions, identify the MDM vendor, locate the enrollment identity, and document paths to MDM bypass (DEP re-enrollment race, beta OS profile, supervised-mode downgrade).
• Persistence via LaunchAgents/Daemons: Install a LaunchAgent plist in ~/Library/LaunchAgents/ (user scope) or /Library/LaunchDaemons/ (system scope, requires root), enumerate competing persistence via KnockKnock, and identify the 50+ persistence locations macOS exposes (login items, Spotlight importers, QuickLook, browser extensions, loginwindow hooks).
• macOS-native malware analysis: Take an unknown Mach-O binary, identify its architecture (file, otool -h), enumerate load commands and linked libraries (otool -L, jtool2 -l), dump entitlements (codesign -d --entitlements -), walk the Objective-C class metadata (otool -ov), disassemble in Hopper/Ghidra, and trace its behavior with fs_usage, opensnoop, dtrace, and an ESF logger.
• Apple Silicon-specific attacks: On M-series Macs, detect PAC enforcement (sysctl kern.bootargs), inspect the sealed system snapshot (mount, csrutil authenticated-root status), test for Rosetta 2 escape paths, and reason about the absence of classic kext-based persistence (System Extensions are user-land).
• Endpoint Security framework instrumentation: Build a minimal ESF client (or use eslogger / ) to subscribe to process-exec, file-write, and login events, and produce a process-tree timeline of attacker behavior on a target Mac — useful both as an attacker (knowing what the defender sees) and a defender (operationalizing ESF for free).

Core Tools

Objective-See Suite (free, open-source, the de facto standard)

Tool	Purpose	Command Example
KnockKnock	Enumerate ~50 macOS persistence locations (LaunchAgents, LaunchDaemons, login items, browser extensions, Spotlight importers, kernel extensions, System Extensions)	KnockKnock.app/Contents/MacOS/KnockKnock -h (or click "Scan")
LuLu	Free open-source macOS firewall — block outbound by bundle ID / binary path	sudo /Objects/LuLu.app/Contents/MacOS/LuLu (mode 2 = block-by-default)
BlockBlock	Persistence monitor — alerts when anything installs a LaunchAgent, login item, or kernel extension	BlockBlock.app (GUI monitor)
OverSight	Camera + microphone monitor — alerts when an app accesses the camera or mic	OverSight.app
TaskExplorer	Process explorer with code-signing info, VT lookups, file/path context	TaskExplorer.app
What's Your Sign?	Finder extension showing code-signing details (cert chain, notarization status)	Right-click → Services → What's Your Sign?

Analysis + Compliance

Tool	Purpose	Command Example
sindresorhus/Equity	Open-source Gatekeeper / notarization / TCC GUI inspector	Equity.app (drag-drop a binary to see signing/notarization details)
mSCP (macOS Security Compliance Project)	NIST + Apple baseline configuration profiles + audit scripts	python3 bin/mSCP.py -s baseline/macos_15_1.yaml
machOView	GUI Mach-O browser — load commands, segments, sections, Objective-C classes	machOView.app (open a Mach-O binary)
Hopper Disassembler	Native macOS disassembler/decompiler (commercial, with demo)	hopper <binary>
Ghidra (Mach-O plugin)	NSA's open-source reverse-engineering suite with Mach-O loader	analyzeHeadless . proj -import <binary>
jtool2	The Swiss-army knife for Mach-O introspection (by Elias Limneos) — replaces many otool workflows	jtool2 -l <binary> (load commands); jtool2 -arch arm64e -L <fat>
ldid	Alternative to codesign for ad-hoc signing with entitlements (Cydia/Telesphoreo origin)	ldid -S<entitlements.plist> <binary>

Methodology

macOS Red Team Five-Phase Workflow

Phase 1          Phase 2          Phase 3          Phase 4          Phase 5
Recon &       →  Privilege &   →  Persistence   →  Credential     →  Defense Bypass
Footold          TCC Posture      (LaunchAgents)    Extraction       & ESF Audit
   │                │                │                │                │
   ▼                ▼                ▼                ▼                ▼
 system_profiler   csrutil status   ~/Library/       security         AMFI bypass,
 sw_vers, uname    tccutil reset    LaunchAgents/     dump-keychain   sandbox profile
 hardware arch     TCC.db audit     LaunchDaemons/    Cookies.        escapes, notarization
 loginwindow       accessibility    login items       binarycookies   conduit abuse,
 MDM profiles      Full Disk Acc    Spotlight imp.    Safari          ESF self-audit
                                                                    via eslogger

Phase 1: Recon & Foothold — Determine the macOS version (sw_vers), hardware architecture (uname -m → arm64/arm64e for Apple Silicon, x86_64 for Intel), system model (system_profiler SPHardwareDataType), FileVault status (fdesetup status), and the user's full name + UID + admin group membership (id, groups). Enumerate installed MDM profiles (profiles list -output user) and the MDM vendor. Identify what security software is running (Look for falcon, sentinelone, jamfProtect, Microsoft Defender processes). Establish a foothold via the engagement scope (existing user creds, a delivered payload, a browser exploit).

Phase 2: Privilege & TCC Posture — Determine SIP status (csrutil status), TCC state (tccutil reset All clears — but only as user; system TCC.db requires root + SIP weakened), and the current process's own TCC grants (via the tccutil reads or by parsing ~/Library/Application Support/com.apple.TCC/TCC.db). Identify entitlement-rich binaries that grant indirect TCC access: Xcode (com.apple.dt.Xcode), Safari (com.apple.Safari), Mail (com.apple.Mail), Terminal with Full Disk Access already granted. Document which TCC-protected resources the user has already granted (the easiest path to credentials and history).

Phase 3: Persistence — Install a LaunchAgent at ~/Library/LaunchAgents/com.example.helper.plist (user scope, runs at user login) or ~/Library/LaunchDaemons/com.example.helper.plist (system scope, runs at boot, requires root + sudo). For wider persistence, consider: login items via LSSharedFileListInsertItemURL, Spotlight importers (~/Library/Spotlight/), QuickLook plugins (~/Library/QuickLook/), browser extensions (~/Library/Application Support/Google/Chrome/Default/Extensions/), the legacy /etc/periodic/daily/ dropboxes, and cron. On Apple Silicon, all of these work — kernel extensions do not.

Phase 4: Credential Extraction — Dump the login keychain via security dump-keychain -d ~/Library/Keychains/login.keychain-db (prompts for user password), enumerate generic passwords (security find-generic-password -l), extract saved Wi-Fi PSKs (security find-generic-password -ga "SSID" -w), parse Safari cookies from ~/Library/Containers/com.apple.Safari/Data/Library/Cookies/Cookies.binarycookies (use binarycookies-reader or python script), and read Safari history from ~/Library/Safari/History.db (Full Disk Access required). Document each credential source and the TCC entitlement required to reach it.

Phase 5: Defense Bypass & ESF Audit — Identify what the defender sees: run eslogger (or build an ESF client) and observe your own actions; understand that ESF is the same data commercial EDR uses. If a specific defender (Falcon, Defender for Endpoint) is running, identify its ESF subscription and any network callouts it makes. Document anti-analysis: AMFI (amfid) checks every exec against the trust cache; sandbox profiles restrict syscalls; Gatekeeper enforces notarization on quarantined files. Document bypasses used: running from non-quarantined paths (no com.apple.quarantine extended attribute), DYLD insertion into TCC-entitled binaries (when SIP permits), entitlement inheritance via signed-and-notarized conduits.

Quick Selection Guide

Scenario	Primary Approach	Alternative
Just got user shell on a Mac	sw_vers, uname -m, id, csrutil status, profiles list	system_profiler SPHardwareDataType
Need to read user documents	Check ~/Library/Application Support/com.apple.TCC/TCC.db for granted Full Disk Access; if absent, look for a TCC-entitled binary to abuse	osascript automation of Finder/TextEdit with prior automation grant
Need credentials	security dump-keychain -d (prompts for user password); security find-generic-password -ga <SSID> -w	chainbreaker for offline hash extraction
Need Safari history	Read ~/Library/Safari/History.db (FDA required)	Parse Cookies.binarycookies for session tokens
Need persistence	LaunchAgent at ~/Library/LaunchAgents/com.example.helper.plist with RunAtLoad=true	Login items via osascript -e 'tell application "System Events" to make login item ...'
Need system-level persistence	/Library/LaunchDaemons/com.example.helper.plist (requires root + signed binary)	System Extension (high detection — not recommended for red team)
Analyzing a Mach-O	file, otool -h (arch), otool -L (libs), codesign -dvvv (signing), jtool2 -l (load commands)	machOView for GUI browsing, Hopper/Ghidra for disassembly
Detecting SIP-bypassed host	csrutil status, nvram boot-args, mount | grep System	csrutil authenticated-root status (Apple Silicon)
Enumerating persistence	Run KnockKnock (GUI), or script: ls -l ~/Library/LaunchAgents/ /Library/LaunchAgents/ /Library/LaunchDaemons/	launchctl list for currently-loaded services

Defense Perspective

Defense Measure	Description
SIP enabled	csrutil status should report "fully enabled". Disable only for development. SIP-protected directories (/System, /usr, /bin, /sbin, preinstalled apps) cannot be modified even by root.
FireVault on + PRK escrow	fdesetup status → "FileVault is On." Recovery key escrowed to MDM or printed and stored. Without FileVault, all on-disk secrets are readable by anyone with physical access.
TCC audit	Quarterly review of /Library/Application Support/com.apple.TCC/TCC.db and ~/Library/Application Support/com.apple.TCC/TCC.db. Alert on any new Full Disk Access or Accessibility grant to a non-Apple binary.
Gatekeeper + notarization enforcement	spctl --status → "assessments enabled." macOS 11+ blocks all downloaded non-notarized apps by default. Users must override explicitly via System Settings → Privacy & Security.
XProtect + MRT active	systemextensionsctl list should show com.apple.XProtect.framework.ScanService and com.apple.MRT. Apple pushes background signature updates silently.
Endpoint Security framework subscription	At least one ESF-based EDR (Jamf Protect, CrowdStrike Falcon, Defender for Endpoint, SentinelOne) deployed via MDM. Apple does not ship a macOS-native EDR — third party is required.
MDM enrollment + restricted profiles	Device supervised via Apple Business/School Manager; MDM profile installed at DEP time; restricted system extensions (only allow-listed team IDs); Gatekeeper and SIP policy enforced via configurationProfile.
Software Update enforcement	softwareupdate --schedule-on; max N-day lag from Apple release; critical security updates auto-installed within 72h.
System Volume sealed snapshot	On Apple Silicon, /System/Volumes/SSV is a sealed snapshot — verify with mount | grep sealed and csrutil authenticated-root status. Tampering here is a hardware-level indicator.

Practical Steps

Detailed payloads in payloads.md, complete test checklist in test-cases.md.

Exercise 1: Enumerate LaunchAgents and LaunchDaemons

# User-scope LaunchAgents (run at login as the user)
ls -l ~/Library/LaunchAgents/ 2>/dev/null
# System-scope LaunchAgents (run at login for any user)
ls -l /Library/LaunchAgents/ 2>/dev/null
# System-scope LaunchDaemons (run at boot as root — highest-impact persistence)
ls -l /Library/LaunchDaemons/ 2>/dev/null
# Apple's own LaunchAgents/Daemons (informational, do not touch)
ls -l /System/Library/LaunchAgents/ /System/Library/LaunchDaemons/ 2>/dev/null

# Inspect one plist
plutil -p ~/Library/LaunchAgents/com.example.helper.plist
# Key fields: Label, ProgramArguments, RunAtLoad, KeepAlive, StartInterval, WatchPaths

# List currently-loaded services
launchctl list | head -20
launchctl list | grep -i example

# Find services that auto-restart (KeepAlive=true)
for f in ~/Library/LaunchAgents/*.plist /Library/LaunchAgents/*.plist /Library/LaunchDaemons/*.plist; do
  [ -f "$f" ] || continue
  plutil -p "$f" 2>/dev/null | grep -q "KeepAlive = 1" && echo "KEEPALIVE: $f"
done

Exercise 2: Extract Keychain Items (with user prompt)

# Show the user's keychains
security list-keychains

# Show all generic-password entries (no secret values)
security dump-keychain ~/Library/Keychains/login.keychain-db | grep -E '"svce"|"acct"|"desc"'

# Dump one item WITH the password (prompts user for keychain unlock)
security find-generic-password -ga "Wi-Fi SSID Name" -d ~/Library/Keychains/login.keychain-db -w
# → password: <WPA-PSK>

# Dump everything (prompts repeatedly for the keychain password)
security dump-keychain -d ~/Library/Keychains/login.keychain-db

# Saved Wi-Fi networks (system keychain)
sudo security find-generic-password -ga "SSID" /Library/Keychains/System.keychain -w

# List certificates (e.g., MDM enrollment identity)
security find-certificate -a /Library/Keychains/System.keychain

Exercise 3: Check SIP and TCC Status

# SIP status (must be run as the logged-in user; shows config)
csrutil status
# Expected on a hardened host: "System Integrity Protection status: enabled."

# Apple Silicon: authenticated-root status (sealed system snapshot)
csrutil authenticated-root status

# TCC: list current grants via the tccutil (limited; full audit requires sqlite3)
tccutil reset All   # DANGEROUS: resets all user TCC grants — only for testing

# Read user TCC.db (sqlite3, requires Full Disk Access for the terminal)
sqlite3 ~/Library/Application\ Support/com.apple.TCC/TCC.db \
  "SELECT service, client, auth_value FROM access ORDER BY service;"
# auth_value: 0=denied, 2=allowed, 3=limited

# System TCC.db (requires root)
sudo sqlite3 /Library/Application\ Support/com.apple.TCC/TCC.db \
  "SELECT service, client, auth_value FROM access ORDER BY service;"

# Which services exist (Apple's documented list — see Apple Platform Security Guide)
# kTCCServiceSystemPolicyAllFiles (Full Disk Access)
# kTCCServiceAccessibility (Accessibility)
# kTCCServiceSystemPolicySysAdminFiles (Administrator files)
# kTCCServiceSystemPolicyDesktopFolder (Desktop)
# kTCCServiceSystemPolicyDocumentsFolder (Documents)
# kTCCServiceSystemPolicyDownloadsFolder (Downloads)
# kTCCServiceCamera, kTCCServiceMicrophone, kTCCServiceLocation, ...

Exercise 4: Mach-O Static Analysis with otool and jtool2

# Architecture (fat binary? single arch?)
file /Applications/Safari.app/Contents/MacOS/Safari
# → Mach-O 64-bit executable [arm64e] (Apple Silicon) or [x86_64]

# Header
otool -h /bin/ls
otool -hv /bin/ls                       # verbose

# Linked libraries
otool -L /bin/ls
# Lists LC_LOAD_DYLIB entries — the dylibs this binary depends on

# Load commands (one line each)
otool -l /bin/ls | head -50
# Or jtool2 (cleaner output):
jtool2 -l /bin/ls

# Symbol table
nm -p /bin/ls | head -20

# Objective-C class metadata (if the binary is Objective-C)
otool -ov /Applications/Safari.app/Contents/MacOS/Safari 2>/dev/null | head -100

# Code-signing details
codesign -dvvv /Applications/Safari.app
codesign -d --entitlements - /Applications/Safari.app
# Look for: Authority (Developer ID / Apple Mac OS Application Signing),
# TeamIdentifier, and entitlements like com.apple.security.cs.* (Hardened Runtime)

# Sections (better in machOView GUI)
jtool2 -section /bin/ls

# Disassemble (Hopper for GUI, jtool2 -d for CLI; arm64e disassembly needs PAC-aware tools)
jtool2 -d --arch arm64e /Applications/Safari.app/Contents/MacOS/Safari

Exercise 5: Enumerate MDM Profiles

# List installed configuration profiles (user-installable)
profiles list -output user

# List all profiles (system; requires admin)
sudo profiles list

# Show details of a specific profile (by identifier)
sudo profiles show -identifier com.example.restrictions

# Show the payload as a plist
sudo profiles show -output open-command -identifier com.example.restrictions > /tmp/profile.plist
plutil -p /tmp/profile.plist

# Where profiles are stored on disk (system)
sudo ls -l /var/db/ConfigurationProfiles/Setup/
sudo ls -l /var/db/ConfigurationProfiles/Settings/

# What's the MDM enrollment identity?
sudo security find-certificate -a -c "Profile" /Library/Keychains/System.keychain
sudo security find-certificate -a -c "MDM" /Library/Keychains/System.keychain

Detection Methods

macOS Endpoint Detection

• SIP (System Integrity Protection) bypass: /usr/bin/csrutil status reports disabled; SIP-protected path modifications.
• TCC (Transparency, Consent, Control) bypass: Apps accessing camera/microphone/location without TCC prompt.
• ESF (Endpoint Security Framework): Apple's native API for endpoint monitoring; eslogger events.
• Keychain access: Unauthorized process accessing user keychain (URLServicesSecret, iCloud).
• Apple Silicon specific: Rosetta anomalies; ARM64e pointer authentication failures.

SIEM Detection Rules

• Splunk SPL (macOS): index=macos sourcetype=osquery:results | where path LIKE "/Library/LaunchAgents/%"
• Jamf Protect / Kandji: Native MDM-integrated EDR for macOS.
• Santa / KnockKnock: Open-source macOS persistence detection.

Defense Evasion Techniques

SIP Bypass

• kext exploitation: Kernel extensions bypass SIP userspace restrictions.
• Recovery mode csrutil disable: Requires physical access; disable SIP persistence.
• Apple Silicon boot policy: Modify boot policy via vuln kext (CVE-2024-23225 class); bypasses SIP.

TCC Bypass

• Bundle ID spoofing: Mimic legitimate app Bundle ID (e.g., com.apple.Safari); inherits TCC entitlements.
• Library validation bypass: Disable library validation; load dylib into signed app.
• Privacy Preferences Policy Control (PPPC) abuse: Modify MDM profile to grant broad permissions.

Keychain Access Stealth

• Use legitimate app signatures: Sign malicious binary with stolen Apple Developer ID; appears as legitimate app.
• Bidirectional keychain abuse: Use keychain to persist credentials; survives user password changes.
• iCloud Keychain sync: Compromise once, sync to all devices.

Apple Silicon Specific

• PAC (Pointer Authentication) bypass: Use CVE in PAC implementation (CVE-2023-32434 class).
• Rosetta translation: Run x86_64 malware under Rosetta; some Apple Silicon monitors miss x86 syscalls.
• M-series specific CVEs: Use unpatched Apple Silicon vulnerabilities before detection rules.

Common Pitfalls

• Treating macOS like Linux: macOS is UNIX-flavored but its security model is layered — SIP protects system volumes, TCC gates user data, AMFI validates every binary at exec, Gatekeeper blocks downloads, and notarization is mandatory. A payload that works on Kali may be silently killed by AMFI on macOS.
• Forgetting about the unified log: every TCC grant, every exec, every network connection is logged to the unified log (log show). Defense teams will see your actions even if no commercial EDR is installed. Tailor your footprint accordingly.
• Assuming SIP is unbreakable: historical CVEs (2019-2024) include SIP bypasses via NFS export (CVE-2019-8805), the crontab DAC override (CVE-2020-3837), and the now-patched writeconfig exploit chain. Always check csrutil status on the target before assuming SIP is enforced.
• Misreading TCC auth_value: 0=denied, 2=allowed, 3=limited. A row with auth_value=2 means the binary HAS the grant — a 0 means the binary was explicitly denied (a useful indicator for "user clicked Don't Allow"). 3 means the grant is scoped (e.g., "limited Photos access").
• Confusing ad-hoc and Developer ID signing: codesign -s - (ad-hoc) is fine for local execution but will NOT pass Gatekeeper on a downloaded file. For a payload delivered via DMG/ZIP, Developer ID + notarization is required. Ad-hoc signing bypasses Gatekeeper only via a non-quarantined delivery path.
• Ignoring Apple Silicon entirely: on M-series Macs, classic ROP/JOP chains often fail because of PAC. Kernel extensions are dead. Rosetta 2 has its own historical bugs. Treat Apple Silicon as a separate target from Intel.
• Assuming csrutil disable is required for everything: most persistence (LaunchAgents/Daemons, login items) and most TCC bypass (DYLD into entitled binaries when SIP is partial) work without disabling SIP. Disabling SIP is a loud, detectable, irreversible-without-reboot action — avoid unless required.
• Forgetting that the user's terminal needs TCC grants: a freshly-spawned reverse shell has no Full Disk Access, no Accessibility, no Automation. The defender's Terminal (or iTerm2) probably has those grants — but the attacker's payload doesn't. Inherit them by spawning into a TCC-entitled binary, or trick the user into granting.

Safety Notes

• Production Macs: any action that writes to /Library/LaunchDaemons/, modifies TCC.db, or enrolls a new MDM profile has blast radius on the user's daily-driver machine. Use a test Mac (or a VMware Fusion / Parallels VM, with snapshots enabled) for active exploitation.
• SIP disabling: csrutil disable requires reboot into Recovery Mode, makes the host vulnerable to much more than the engagement intended, and persists until explicitly re-enabled. Document the change; re-enable before handoff.
• Keychain dump: security dump-keychain -d repeatedly prompts the user for their login password. On a production machine this immediately tips off the user. Capture once, in a controlled test environment.
• Cookies.binarycookies extraction: these cookies include live session tokens for banking, SSO, and email. Treat them as credentials: store encrypted, do not commit to git, discard post-engagement.
• ESF logging: a custom ESF client generates substantial log noise and consumes the client's MDM-allowed ESF slot (only one ESF subscriber per process per Apple's policy, though multiple processes can subscribe). Confirm with the customer before installing one on a production Mac.
• MDM profile installation: installing a malicious profile on a customer-managed Mac may conflict with the existing MDM and trigger Jamf/Intune alerts. Document and use a test machine.
• Code signing certificate handling: never commit a Developer ID certificate + private key to a repo. Use Apple's notarytool with an app-specific password stored in the macOS keychain (xcrun notarytool store-credentials), not in env vars.

Hacker Laws

• Trust but Verify — csrutil status reports "enabled" but on some hosts the authenticated-root is not sealed, or a single SIP-protected path has been weakened. Verify with csrutil authenticated-root status, mount | grep sealed, and by attempting a write to /System.
• Defense in Depth — SIP, TCC, AMFI, sandbox, Gatekeeper, notarization, XProtect, MRT, ESF-based EDR, FileVault, Secure Boot. No single layer stops a determined attacker; the stack slows them and produces telemetry at each layer.
• Assume Breach — Design your monitoring assuming the attacker has user-level access. The unified log records every TCC grant, every exec, every network connection — but only if you forward it to a SIEM and alert on anomalies. Apple ships the data; the operationalization is your job.
• Least Privilege — A user should not have Full Disk Access to every app. A binary should not run with com.apple.security.cs.disable-library-validation unless absolutely required. Every entitlement is an attack surface. Audit codesign -d --entitlements - on every binary in ~/Library/LaunchAgents/.
• Supply Chain Trust — Every macOS binary in the trust cache, every Developer ID certificate, every notarization ticket, every MDM-pushed configuration profile is a supply chain link. A revoked Developer ID (e.g., Apple's 2019 revocation of Facebook's and Google's enterprise certs) propagates instantly to every Mac that has checked revocation.
• Minimize Attack Surface — Disable Java in the browser (gone in modern Safari but still enforced via MDM), block unsigned extensions, restrict System Extensions to allow-listed team IDs, disable the root account (dsenableroot -d), disable SSH unless needed, disable Remote Login and Screen Sharing.
• Information Wants to Be Free — Keychain contents, Cookies.binarycookies, Safari History.db, the unified log, ~/Library/Application Support/ — these are credentials and history in plain sight on every Mac. FileVault protects them at rest only; a logged-in user is a wide-open book.
• Weakest Link Is Human — Most macOS compromises start with a fake Flash update (Shlayer's classic lure), a pirated app DMG (Bundlore), a malicious Office macro (OfficeMacros are rare but exist), or a socially-engineered notarized dropper. User education, Gatekeeper enforcement, and blocking known-malicious Developer IDs via MDM are the defenses.

Apple Silicon Security Architecture

Apple Silicon (M1/M2/M3/M4) fundamentally reshapes the macOS attack surface. The kernel and Apple-signed system binaries run arm64e with Pointer Authentication Codes (PAC) on every function pointer and return address, defeating most classic ROP/JOP chains. The system volume is a cryptographically sealed APFS snapshot (SSV — Signed System Volume), verified at every boot by the boot ROM and the kernel. Third-party kernel extensions are effectively dead; the supported path is System Extensions (user-land) and DriverKit. Rosetta 2 (x86_64 emulation) is a separate ABI with its own historical bugs (CVE-2021-30717 — Rosetta translation bypassed code signing checks). The Page Protection Layer (PPL) on M1+ protects page tables and code-signing metadata from kernel-mode tampering — even a kernel read/write primitive cannot forge entitlements or trust-cache entries.

Boot Chain

1. Boot ROM — immutable, masked ROM in the SoC; verifies the next stage via Apple's Root CA.
2. Secure Enclave (SEP) — holds device-specific keys; runs sepOS, a separate L4 microkernel.
3. iBoot — verifies the kernel cache and Device Tree; loads the kernel.
4. Kernel + Kexts / System Extensions — kernel runs arm64e on Apple Silicon; executes launchd (PID 1).
5. Signed System Volume (SSV) — / is a sealed APFS snapshot; mount shows apfs,sealed,read-only. Firmlinks (/usr/share/firmlinks) bridge read-write paths to /System/Volumes/Data.

Pointer Authentication Codes (PAC)

ARMv8.3 introduces PAC. Every function pointer and return address can be cryptographically signed with a 128-bit modifier and a secret key. Instructions: pacia/pacib (sign), autia/autib (authenticate), retaa/retab (authenticated return), braa/blraa (authenticated branch). Apple-signed binaries use arm64e; third-party code runs arm64 (PAC-disabled). Exploitation requires forging a PAC signature or finding a PAC bypass (signing oracle, exception-stream abuse, JIT spray against PAC-disabled regions).

Page Protection Layer (PPL)

PPL is an exception level below the kernel (EL2 on Apple Silicon, loosely). It guards: page table entries for executable mappings, the trust cache (kernel-resident CDHash list), code-signing blob interpretation, and the kernel's apple_sep Industriously primitives. Even with a kernel read/write primitive, you cannot self-sign an entitlement without breaking PPL. Documented PPL research: the "PPL爆破" / PPL bypass literature (2023-2024) explores hardware fault injection but no software-only PPL break is publicly known as of 2026.

Kexts vs System Extensions

• Kernel extensions (kexts) — legacy; tagged .kext, run in kernel space. Effective death: macOS 11 Big Sur requires notarized kexts with com.apple.developer.kextallow entitlement (Apple-issued only). Loading requires kextload + reboot + User-Approved MDM. Most third-party kexts (Little Snitch, Little Flocker — now built into LuLu, VirtualBox, kCores) shipped System Extension replacements by 2023.
• System Extensions (SE) — user-land, sandboxed, communicate with the kernel via a private IPC. Three categories: Endpoint Security (ESF — EDR), Network Extension (NEFilterProvider — firewall/VPN), DriverKit (user-space drivers for USB, audio, networking, HID).

Endpoint Security Framework Internals

ESF (EndpointSecurity.framework) is the only Apple-blessed API for system telemetry on macOS 10.15+. It is a Mach-based IPC between a System Extension (client) and the kernel (endpoint). A client subscribes to event types, receives messages containing the event details + audit tokens for the actor processes, and can issue responses (authorize/deny) for certain event classes.

Event Categories

• EXEC — process start. Fields: executable path, args, env, parent PID, audit token.
• EXIT — process end. Fields: exit status, signal.
• OPEN / OPEN_EXTENDED — file open. Fields: path, flags, mode.
• WRITE / RENAME / UNLINK / TRUNCATE — file mutation.
• MOUNT / UNMOUNT — filesystem events.
• AUTHENTICATION — OpenDirectory auth (login, password change).
• LOGIN_LOGOUT — loginwindow session events.
• CLONE / COPYFILE — APFS-specific file operations.
• CS_OPS / TASK_INSPECT — code-signing operations and task inspection (debugger attach).

Client Lifecycle

1. es_new_client(&client, &handler) — create client. Requires com.apple.developer.endpoint-security.client entitlement (Apple-issued for EDR vendors; ad-hoc signing with this entitlement requires boot-args amfi_get_out_of_my_way=1 or SIP-disabled).
2. es_subscribe_client(client, events, count) — register interest.
3. Handler receives es_message_t *. The handler must call es_respond(result, msg, auth_result) for auth events; clear messages are fire-and-forget.
4. es_mute_path / es_mute_path_prefix — exclude paths (e.g., /System/Library/).
5. On macOS 13+: es_clear_cache() — required periodically to drain the kernel's message buffer.

Tooling

• eslogger — built-in CLI (macOS 13+) for one-shot event capture: sudo eslogger exec open write > /tmp/esf.log.
• ESF clients on GitHub: esf-client, nested-objc, ZicoMonitor, Santa (Google) — all open-source reference implementations.
• Apple's EndpointSecurity framework docs: see developer.apple.com/documentation/endpointsecurity.

MDM Control Plane

Mobile Device Management is the enterprise control plane for macOS in 2026 — Jamf, Kandji, Microsoft Intune, Workspace ONE, Addigy, Mosyle. MDM pushes configuration profiles (Apple's .mobileconfig format) that enforce restrictions, push certificates, configure FileVault, deploy System Extensions, and remotely wipe. Supervision via Apple Business/School Manager (DEP — Device Enrollment Program, now Apple Automated Device Enrollment) makes profiles non-user-removable.

Profile Anatomy

A .mobileconfig is a signed plist with PayloadContent, PayloadIdentifier, PayloadType, PayloadUUID, PayloadDisplayName, and a signature (CMS/PKCS#7). Payload types include com.apple.applicationaccess (restrictions), com.apple.security.FDE (FileVault), com.apple.system-extension-policy (allow-listed SE Team IDs), com.apple.security.firewall (application firewall), com.apple.networkextension.configuration (VPN/filtered-network), com.apple.ldap.account (directory binding).

Enrollment Modes

• User-initiated — user opens profiles install -path foo.mobileconfig or taps enroll in System Settings. Profiles are user-removable.
• DEP / Automated Device Enrollment — supervised out-of-box; profiles are non-removable; recovery partition re-enrolls.
• Account-Driven User Enrollment (macOS 13+) — managed Apple ID at login; only the user's iCloud Drive container is managed. Lower blast radius.

MDM Abuse Vectors

1. Enrollment identity theft — extract the MDM identity cert from /Library/Keychains/System.keychain, enroll rogue devices impersonating the supervised Mac.
2. DEP re-enrollment race — wipe a supervised Mac, race to enroll in a different MDM before DEP check-in completes.
3. Beta OS profile bypass — install a beta macOS profile that bypasses some restriction enforcement.
4. Supervised-mode downgrade — older macOS versions had downgrade paths; modern macOS is largely closed.
5. MDM server compromise — compromise the Jamf/Intune server → push malicious profiles fleet-wide (highest-impact scenario).

Real-World macOS Threats

macOS malware from 2017 to 2026 illustrates how attackers adapt to the platform's defenses. Key families:

Adware / Dropper Wave (2017-2020)

• Shlayer (2019-2022) — the dominant macOS malware family by volume. Disguised as a fake Flash updater or pirated app DMG. Initially signed with a stolen/throttled Developer ID; later notarized (the notarized-dropper model: a notarized parent fetches the unnotarized payload). Persistence via LaunchAgent in ~/Library/LaunchAgents/.
• Bundlore (2018-2020) — adware dropper, similar delivery model. Multi-arch fat binary (x86_64 + arm64e) after Apple Silicon launched.
• CoinMiner (2018+) — XMRig-based cryptominer. Often delivered via pirated Adobe Creative Cloud DMGs. LaunchDaemon for boot-time mining.

Apple Silicon Transition (2021-2022)

• Silver Sparrow (Feb 2021) — the first malware observed shipping an arm64 payload (alongside x86_64). Distributed via the Apple Developer ID RA Thompson and installed via a package (update.pkg). The payload (inspector) was never observed doing anything beyond beaconing — a "warhead" that was never fired. Documented by Red Canary.

Modern Stealer Wave (2023-2026)

• XCSpy (2023) — XCSBuild-disguised stealer targeting Apple developers. Malicious Xcode project files that ran osascript payloads on project open. Stole iCloud tokens and Keychain items.
• NodeStealer (2023) — JavaScript-based stealer distributed via fake browser updates. Originally Windows-targeting; ported to macOS in 2023. Exfiltrated cookies and saved passwords from Chrome, Brave, Safari.
• Atomic Stealer / AMOS (2024-2025) — sold on Russian cybercrime forums for ~$1k/month subscription. Targets Safari cookies, Chrome cookies, Keychain, cryptocurrency wallets (Electrum, Exodus, MetaMask), and exfiltrates via Telegram bots.
• Cthulhu Stealer (2024) — copycat of Atomic; same target surface, slightly different exfil. Distributed via cracked-game DMGs.

Nation-State / Targeted

• Pegasus ( Citizen Lab, multiple variants) — NSO Group iOS spyware; macOS variant reported in 2022 targeting activists via zero-click iMessage delivery.
• Predator (Cytrox / Intellexa) — commercial spyware; macOS variant reported in 2023.
• DazzleSpy / OSX.WolfsBane (2024) — water-hole attacks on pro-democracy activists in Hong Kong via Safari WebKit zero-day.

macOS Forensic Artifacts

macOS produces unusually rich forensic telemetry. Unlike Windows (Event Log) or Linux (syslog/journald), macOS records to the unified log — a binary, time-indexed, structured log stream that requires log show to parse. Combined with the TCC.db, Keychain, FSEvents, and Spotlight metadata, an IR analyst can reconstruct nearly every action an attacker took.

Primary Artifact Sources

Artifact	Path	Content
Unified log	/var/db/diagnostics/ (binary)	All system telemetry since macOS 10.12 Sierra; structured subsystem/category
TCC.db (user)	~/Library/Application Support/com.apple.TCC/TCC.db	Privacy grants (Full Disk Access, Camera, Microphone, etc.)
TCC.db (system)	/Library/Application Support/com.apple.TCC/TCC.db	System-scope privacy grants
Keychain (user)	~/Library/Keychains/login.keychain-db	User credentials (Safari, Wi-Fi, app tokens, certs)
Keychain (system)	/Library/Keychains/System.keychain	System secrets (MDM identity, Wi-Fi PSKs, system certs)
Cookies.binarycookies	~/Library/Containers/com.apple.Safari/Data/Library/Cookies/	Safari session cookies (binary plist)
History.db	~/Library/Safari/History.db	Safari browsing history (SQLite)
FSEvents	/.fsevents/*	Filesystem events (creates, deletes, renames)
Spotlight metadata	/.Spotlight-V100/Store-V2/	File content index (may contain path + metadata of deleted files)
quarantine	xattr -l <file> → com.apple.quarantine	Downloaded-file provenance (browser, timestamp)
launchd state	/var/db/launchd.db/, ~/Library/LaunchAgents/	Persistence items
mdmcache	/var/db/ConfigurationProfiles/	MDM profile payloads

Unified Log Hunting

# Recent process exec events (subsystem = com.apple.securityd logs exec)
sudo log show --predicate 'subsystem == "com.apple.securityd"' --last 1h --style compact

# All TCC-related events (every privacy grant, denial, prompt)
sudo log show --predicate 'subsystem == "com.apple.TCC"' --last 24h

# Code-signing failures (AMFI denials)
sudo log show --predicate 'subsystem == "com.apple.amfi"' --last 24h --info --debug

# Search the entire unified log for a binary path (post-compromise)
sudo log show --last 7d --info --debug | grep -F "/tmp/payload"

Apple Platform Security Layers

Apple's published Platform Security Guide (the authoritative reference) defines the layered trust model. From hardware to user:

Layer	Component	Purpose
Hardware	Boot ROM, SEP, TouchID/Touch Bar	Immutable root of trust; biometric secrets
Boot	iBoot, kernel cache, SSV	Verified boot chain; sealed system volume
Kernel	AMFI, sandbox (sandboxd), AppleMobileFileIntegrity	Binary validation at exec; syscall filtering; entitlement enforcement
System services	launchd, tccd, securityd, logd, mdmclientd	PID-1 supervisor; TCC daemon; keychain daemon; log daemon; MDM agent
Frameworks	EndpointSecurity.framework, Security.framework, LocalAuthentication.framework	Apple-blessed APIs for telemetry, keychain, biometric auth
Userspace	tccd, mdmclientd, EDR System Extensions, browsers, apps	The attack surface most red teamers care about

The trust flows top-down: hardware verifies boot chain verifies kernel verifies system binaries verifies userspace. A break at any layer subverts layers above. SIP and SSV together make layer 2 (boot) and layer 3 (kernel) very hard to subvert on modern Apple Silicon; most practical attacks target layer 5-6 (userspace and apps).

Detection Engineering

For defenders building macOS detection (or for red teamers modeling what defenders see), the layered telemetry stack enables layered detection:

Layer 1: Process Telemetry (ESF exec events)

• Suspicious parent-child relationships: bash → curl → bash (stager pattern), Word → bash (macro), Safari → osascript (drive-by AppleScript).
• Suspicious binary paths: anything under /tmp/, /var/tmp/, ~/Library/Application Support/<random>/, ~/Library/.foo/.
• Recurring binary names: update_agent, helper, mdworker32, searchd (typosquatting on mdworker, mds, searchd).

Layer 2: File Telemetry (ESF write, rename, unlink)

• LaunchAgent / LaunchDaemon writes: any write to ~/Library/LaunchAgents/ or /Library/LaunchDaemons/ by a non-installer process.
• TCC.db writes: direct sqlite INSERT to the TCC.db is highly abnormal — only tccd should write.
• Browser cookie access: a non-browser process reading Cookies.binarycookies is a stealer.
• Keychain reads: security CLI reading the login keychain from a non-Terminal/iTerm process.

Layer 3: Network Telemetry

• Outbound C2 patterns: connections to dynamic DNS (*.duckdns.org, *.noip.com), Tor exit nodes, known-bad ASNs.
• DNS beaconing: periodic DNS queries to the same domain at fixed intervals.
• TLS JA3/JA4 fingerprints: map known macOS malware JA3 hashes.

Layer 4: Behavior Indicators

• Rapid enumeration commands: id, whoami, hostname, ifconfig, system_profiler executed in <2s.
• Credential access patterns: security dump-keychain followed by curl to an external host.
• Persistence immediately after download: a downloaded DMG-mount → LaunchAgent-install sequence within minutes.

Lab Build Guide

A reproducible macOS test lab is essential — never test live exploits on a daily-driver Mac. Recommended stack:

Tier 1: Virtual Machines (free, snapshots)

• VMware Fusion Pro 13+ (free for personal use since May 2023): full Apple Silicon support. Snapshots are essential — roll back between tests.
• Parallels Desktop (commercial): faster than VMware on Apple Silicon, but paywalled.
• UTM (free, open-source): QEMU-based; supports both Intel macOS (slow, x86 emulation) and Apple Silicon native hypervisor (fast).
• Apple's ipsw (Restore image): download via ipsw download app --latest-version (or from IPSW Downloads) for VM creation.

Tier 2: Bare-Metal Test Mac

• A dedicated Mac mini or MacBook for malware detonation.
• Install fresh from Recovery (Cmd+R Intel, hold power Apple Silicon).
• Enable FileVault to test post-FDE exploitation.
• Snapshot the APFS volume: diskutil apfs createSnapshot /.
• Wipe between engagements (diskutil eraseDisk).

Tier 3: MDM Test Environment

• Apple Business Manager + Jamf Now (free up to 3 devices): for testing MDM profile delivery, supervision, and DEP workflows.
• Addigy / Kandji / Mosyle free trials: 30-day evaluations; useful for cross-vendor MDM testing.
• MicroMDM (open-source): community MDM server for profile push testing without vendor dependencies.
• SCEP / ADCS test cert: for testing certificate enrollment.

Lab Hygiene

• Isolated network: VLAN or dedicated SSID; no access to corporate resources.

• DNS sinkhole (Pi-hole or NextDNS): block known-malicious C2 during detonation.

• Network capture: persist tcpdump or zeek to capture C2 traffic for later analysis.

• INetSim / FakeNet-NG: simulate C2 servers for detonation.

• Snapshots before each test: VM snapshot or tmutil localsnapshot for APFS.

• vs mobile-security — mobile-security is iOS/Android at the application layer: app review, certificate pinning bypass, APK/IPA reverse engineering, mobile data protection. THIS skill is macOS desktop/laptop at the OS and platform layer: SIP/TCC/AMFI/ESF, LaunchAgents/Daemons persistence, Mach-O analysis, Keychain (desktop variant), MDM as enterprise control plane. The Apple Silicon transition (2020-2022) further differentiates the two: macOS on M-series is a desktop Unix with arm64e + PAC + sealed snapshots; iOS has had arm64e longer and has additional sandbox restrictions (no shell, no Terminal, no osascript).

• vs av-edr-evasion — av-edr-evasion focuses on Windows Defender and commercial EDR (CrowdStrike, SentinelOne, Defender for Endpoint) with techniques like direct syscalls, process doppelgänging, and DLL hollowing. THIS skill focuses on the macOS-specific defense stack (AMFI, Gatekeeper, XProtect, MRT, TCC, sandbox profiles) and the macOS-native EDR surface (ESF, System Extensions). Where av-edr-evasion covers Windows API abuse, this skill covers Mach API abuse, entitlement inheritance, and signed-and-notarized dropper patterns.

• vs binary-reverse — binary-reverse covers PE, ELF, and Mach-O statically and dynamically — broadly platform-agnostic. THIS skill narrows to Mach-O specifically and the macOS-binary ecosystem: entitlements, Objective-C metadata, Swift symbol mangling, arm64/arm64e disassembly (with PAC-aware tooling), the LC_LOAD_DYLIB chains, the trust cache, and the interaction between code signing and AMFI at exec time.

• vs digital-forensics — digital-forensics covers IR artifacts broadly. THIS skill covers macOS-specific artifacts: the unified log (log show), FSEvents (/.fseventsd), Spotlight metadata (.metadata_core), TCC.db audit, Keychain access history, secure notes, and Safari history/cookies. The macOS forensic surface is unusually rich but uniquely structured.

Cross-References

• skills/mobile-security/SKILL.md — iOS/Android application security. Shares code-signing concepts (codesign, ldid, entitlements) but the attack surface is otherwise different.
• skills/binary-reverse/SKILL.md — Static/dynamic analysis broadly. The Mach-O sections there are the platform-agnostic version; this skill provides macOS-specific tooling (otool, jtool2, machOView, codesign, etc.).
• skills/av-edr-evasion/SKILL.md — AV/EDR evasion (Windows-centric). The macOS analog is here: AMFI, Gatekeeper, XProtect, MRT, TCC, ESF.
• skills/digital-forensics/SKILL.md — Forensic artifact analysis broadly. The macOS-specific artifacts (unified log, FSEvents, TCC.db, Keychain, Cookies.binarycookies) live in this skill.
• skills/anti-forensics/SKILL.md — Cleanup techniques. The macOS-specific cleanup (LaunchAgent removal, TCC reset, keychain item rotation) lives in this skill.
• skills/post-exploitation/SKILL.md — General post-exploitation activities. The macOS-specific persistence (LaunchAgents/Daemons, login items, Spotlight importers) is here.
• skills/pentest-reporting/SKILL.md — Structuring the deliverable. macOS findings map to MITRE ATT&CK for macOS (which is a fully-supported platform in ATT&CK).
• skills/scada-ics-security/SKILL.md — Industrial control systems. Not directly related, but some Mac-based engineering workstations in OT environments warrant macOS-specific hardening (rare).
• skills/identity-attack/SKILL.md (if present) — Cross-platform identity attacks. macOS-bound identities (Keychain certificates, MDM enrollment identity, CloudKit) are covered here.

Learning Resources

• This skill's supplementary files: payloads.md, test-cases.md
• Deep-dive guide: guides/macos-security-playbook.md — end-to-end operational playbook covering macOS security architecture, Apple Silicon specifics, building a test lab, red team methodology, real-world macOS threats (XCSpy, Shlayer, Bundlore, Silver Sparrow, NodeStealer, CoinMiner), defense patterns, and references.
• Reference repositories (the inspirations for this skill):
  • Objective-See tools (KnockKnock, LuLu, BlockBlock, OverSight, TaskExplorer, What's Your Sign?): github.com/objective-see
  • macOS-Security-and-Privacy-Guide (drduh, 20k+ stars): github.com/drduh/macOS-Security-and-Privacy-Guide
  • macOS Security Compliance Project (mSCP, NIST + Apple): github.com/usnistgov/macos_security
  • sindresorhus/Equity (Gatekeeper/notarization inspector): github.com/sindresorhus/Equity
  • How-to-Use-Your-Security-Tools-on-macOS: various community guides
  • machOView: github.com/gdbinit/machOView
  • jtool2 (Elias Limneos): newosxbook.com/tools/jtool.html
  • ldid (Jay Freeman / saurik): github.com/saurik/ldid
  • ESF demos (0xcpu gist): gist of a minimal ESF client in C
• External resources:
  • Apple Platform Security Guide: support.apple.com/guide/security/welcome/web
  • Apple Developer — Code Signing Guide: developer.apple.com/library/archive/documentation/Security/Conceptual/CodeSigningGuide
  • Apple Developer — Endpoint Security Framework: developer.apple.com/documentation/endpointsecurity
  • Apple Developer — Hardened Runtime: developer.apple.com/documentation/security/hardened_runtime
  • Objective-See blog (Patrick Wardle's research): objective-see.org/blog.html
  • Patrick Wardle's talks (DEF CON, OBTS, Black Hat): objective-see.org/downloads.html — "The Cost of Insecurity", "Death by 1000 Installers", "Bypassing Bounds Checker", etc.