offensive-windows-boundaries
This skill provides a taxonomy and enumeration methodology for Windows security boundaries including kernel/user mode separation, sandbox architectures like AppContainer and LPAC, COM/RPC interfaces, and hypervisor isolation. Use it when planning privilege escalation chains, analyzing sandbox escape vectors, or designing attacks that must cross Windows trust boundaries and security policies.
git clone --depth 1 https://github.com/SnailSploit/Claude-Red /tmp/offensive-windows-boundaries && cp -r /tmp/offensive-windows-boundaries/Skills/infrastructure/offensive-windows-boundaries ~/.claude/skills/offensive-windows-boundariesSKILL.md
# SKILL: Week 7: Defeating Windows Security Boundaries
## Metadata
- **Skill Name**: windows-boundaries
- **Folder**: offensive-windows-boundaries
- **Source**: https://github.com/SnailSploit/offensive-checklist/blob/main/7-windows-boundaries.md
## Description
Windows security boundary taxonomy and attack surface enumeration: kernel/user boundary, sandbox boundaries (LPAC, AppContainer), COM/RPC boundaries, hypervisor boundary, trust level transitions. Use when planning privilege escalation paths, sandbox escapes, or understanding Windows security architecture.
## Trigger Phrases
Use this skill when the conversation involves any of:
`Windows boundaries, security boundary, kernel user boundary, sandbox escape, AppContainer, LPAC, COM boundary, RPC boundary, hypervisor, Hyper-V, privilege escalation, trust level`
## Instructions for Claude
When this skill is active:
1. Load and apply the full methodology below as your operational checklist
2. Follow steps in order unless the user specifies otherwise
3. For each technique, consider applicability to the current target/context
4. Track which checklist items have been completed
5. Suggest next steps based on findings
---
## Full Methodology
# Week 7: Defeating Windows Security Boundaries
## Overview
_created by AnotherOne from @Pwn3rzs Telegram channel_.
Week 6 taught you how mitigations work defensively.
You'll learn to bypass the OS security _policies and features_ that prevent your code from running, your processes from accessing protected resources, and your actions from being logged.
This is distinct from Week 8, which teaches you how to bypass _exploit mitigations_ (DEP, ASLR, CFG) once your code is already running.
> **Week 7 vs Week 8 - The Key Distinction**:
>
> - **Week 7** answers: _"Can my code execute at all?"_ - bypass AMSI, WDAC, ASR, AppContainers, integrity levels, PPL, ETW telemetry
> - **Week 8** answers: _"Can my exploit succeed?"_ - bypass DEP, ASLR, stack cookies, CFG/XFG, heap safe-unlinking
**This Week's Focus**:
- Offensive reconnaissance and mitigation fingerprinting
- AMSI bypass and script-based attack techniques
- Protected Process Light (PPL) exploitation
- Sandbox, integrity level, and AppContainer bypass
- WDAC and Attack Surface Reduction (ASR) bypass
- ETW manipulation and telemetry blinding
- Kernel driver interaction fundamentals (preparation for Week 11)
**Prerequisites**:
- Completed Week 6: Understanding Modern Windows Mitigations
- Week 5: Basic exploitation techniques (stack overflow, ROP, heap)
- Familiarity with WinDbg, x64dbg, and IDA/Ghidra
- C/C++, Python, and assembly knowledge
### Week 7 Deliverables
By the end of this week, you should have completed:
- [ ] **Recon Tool**: Built a mitigation fingerprinting tool
- [ ] **AMSI Bypass**: Implemented working AMSI bypass techniques
- [ ] **PPL Research**: Documented PPL bypass vectors
- [ ] **Sandbox Escape**: Bypassed AppContainer or integrity level restrictions
- [ ] **WDAC/ASR Bypass**: Demonstrated at least one WDAC and one ASR bypass
- [ ] **ETW Blinding**: Implemented ETW provider patching to suppress telemetry
- [ ] **Driver IOCTL Lab**: Loaded a test driver, sent an IOCTL, set a kernel breakpoint (Week 11 prep)
## Day 1: Offensive Reconnaissance & Mitigation Fingerprinting
- **Goal**: Master target enumeration - fingerprint system and process mitigations to identify attack vectors.
- **Activities**:
- _Reading_:
- [Windows Exploit Protection](https://learn.microsoft.com/en-us/microsoft-365/security/defender-endpoint/exploit-protection-reference) - Official mitigation documentation
- [Process Mitigation Policies](https://learn.microsoft.com/en-us/windows/win32/api/processthreadsapi/nf-processthreadsapi-getprocessmitigationpolicy)
- [Override Process Mitigations via Policy](https://learn.microsoft.com/en-us/windows/security/operating-system-security/device-management/override-mitigation-options-for-app-related-security-policies)
- _Online Resources_:
- [DEFCON 27 - Exploiting Windows Exploit Mitigation for ROP Exploits](https://www.youtube.com/watch?v=gIJOtP1AC3A)
- [Sandbox Mitigations](https://troopers.de/media/filer_public/f6/07/f6076037-85e0-42b7-9a51-507986edafce/the_joy_of_sandbox_mitigations_export.pdf)
- [Offensive Windows Internals](https://github.com/matthieu-hackwitharts/Win32_Offensive_Cheatsheet)
- _Tool Setup_:
- Process Hacker / System Informer
- WinDbg Preview with mitigation inspection scripts
- PE-bear / pestudio for binary analysis
- _Exercise_:
- Build comprehensive mitigation scanner
- Enumerate all protected processes on target
- Identify legacy/unprotected binaries for exploitation
### Deliverables
- [ ] Build a comprehensive mitigation scanner
- [ ] Fingerprint process-level protections remotely
- [ ] Identify unprotected/legacy binaries on target
- [ ] Map kernel mitigation status
### Target Mitigation Landscape
```text
┌─────────────────────────────────────────────────────────────────┐
│ Offensive Reconnaissance: What to Enumerate │
├─────────────────────────────────────────────────────────────────┤
│ │
│ SYSTEM-LEVEL PROCESS-LEVEL │
│ ───────────── ───────────── │
│ ┌──────────────┐ ┌──────────────┐ │
│ │ VBS/HVCI │ │ DEP/NX │ │
│ │ WDAC/CI │ │ ASLR │ │
│ │ Secure Boot │ │ CFG/XFG │ │
│ │ Credential │ │ CET/Shadow │ │
│ │ Guard │ │ ACG │ │
│ │ KDP │ │ CIG │ │
│ │ KASLR │ │ Child Process│ │
│ └──────────────┘ └──────────────┘ │
│ │Active Directory attack methodology for internal network red team engagements. Covers reconnaissance (BloodHound, PowerView, ADExplorer), credential abuse (Kerberoasting, ASREProasting, NTLM relay, LLMNR/NBT-NS poisoning), privilege escalation (ACL abuse, GPO abuse, unconstrained/constrained delegation), lateral movement (Pass-the-Hash, Pass-the-Ticket, Overpass-the-Hash, WMI/WinRM/PsExec), persistence (Golden/Silver/Diamond Tickets, DCSync, DCShadow, AdminSDHolder, Skeleton Key), forest trust attacks, ADCS abuse (ESC1-ESC15), and modern MDI/Defender for Identity evasion. Use when assessing on-prem AD, hybrid AD/Entra ID environments, or ADCS deployments.
Comprehensive red team operations methodology covering full engagement lifecycle from planning through reporting. Addresses engagement scoping and rules of engagement negotiation, multi-tier C2 infrastructure design with redirectors and domain fronting, malleable traffic profiles and beacon tradecraft, OPSEC discipline including attribution avoidance and indicator management, EDR and AMSI evasion techniques using direct syscalls and unhooking, data collection with chain-of-custody controls, and structured reporting with purple team debrief workflows. Covers assumed-breach, external-to-internal, insider threat, and hybrid physical-cyber engagement scenarios with MITRE ATT&CK mapping throughout. Targets operators planning or executing adversary simulation engagements against mature defenders.
Anti-forensics and evidence destruction techniques for red team operators conducting authorized engagements. Covers log clearing on Windows (wevtutil, Clear-EventLog, ETW provider patching) and Linux (journal truncation, utmp/wtmp binary editing, syslog manipulation), timestamp manipulation via Timestomp and SetMACE to defeat timeline analysis, filesystem-level anti-forensics including NTFS Alternate Data Streams for payload hiding and secure deletion with sdelete/shred, memory artifact removal to counter live forensics, disk artifact manipulation targeting MFT entries and USN journal records, network forensics evasion through encrypted C2 channels and DNS-over-HTTPS tunneling, and anti-VM/sandbox detection to avoid dynamic analysis environments. Tools: Timestomp, wevtutil, sdelete, shred, MimiPenguin, Invoke-Phant0m. Aligns to MITRE ATT&CK T1070 (Indicator Removal), T1027 (Obfuscated Files or Information), T1497 (Virtualization/Sandbox Evasion). Each technique includes the forensic artifact it targets, the destruction or manipulation method, and the defender perspective so operators understand detection gaps they must account for.
Advanced API exploitation methodology focused on business logic abuse and sophisticated attack patterns that bypass traditional security controls. Covers business logic bypass through API call chaining and workflow manipulation. Addresses GraphQL-specific attacks including batching for credential brute-force, query depth exploitation, and introspection abuse. Includes pagination exploitation for data exfiltration, webhook hijacking for SSRF and data interception, and resource exhaustion through algorithmic complexity attacks. Covers race conditions in API transactions using parallel request techniques. Provides comprehensive JWT manipulation including algorithm confusion, kid injection, jku/x5u abuse, and claim tampering. Details API key leakage detection across source repositories, client-side code, and error messages. Covers undocumented endpoint discovery through predictable naming, debug routes, and source map analysis. Tooling includes Arjun, ParamSpider, jwt_tool, and GraphQL Voyager. Designed for authorized penetration testers targeting business logic layers that automated scanners miss.
Comprehensive API security testing methodology covering REST, gRPC, and WebSocket attack surfaces. Addresses the full OWASP API Security Top 10 2023 including BOLA/IDOR, broken authentication, excessive data exposure, rate limiting bypass, BFLA, mass assignment, SSRF, and security misconfiguration. Includes REST-specific attacks such as HTTP verb tampering, content-type switching, and parameter pollution. Covers gRPC exploitation through protobuf interception, reflection API enumeration, and metadata injection. Addresses WebSocket vulnerabilities including origin bypass, message injection, and cross-site WebSocket hijacking. Provides tooling guidance for Burp Suite, Postman, grpcurl, websocat, and mitmproxy. Each technique includes detection signatures and defensive indicators so you understand what artifacts your testing leaves behind. Designed for authorized penetration testing engagements against API-driven architectures.
Bluetooth Low Energy (BLE) attack methodology — GATT enumeration, characteristic read/write without auth, pairing downgrade (Just Works forced), LE Secure Connections bypass, MITM via active relay, sniffing with Sniffle (TI CC1352) / Ubertooth / Frontline, encryption key extraction (LE Legacy Pairing crackable, LE Secure Connections strong), proximity authentication abuse (cars, locks), and companion-app trust analysis. Use for IoT BLE devices, smart locks, fitness trackers, medical devices, BLE beacons, or any device pairing over BLE.