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Red Teaming 101: Master Index

BLUF: This series provides a structured roadmap for transitioning from traditional penetration testing to advanced red team operations using the Harada OW64 methodology.

Important

Authorized use only: Use these notes only in owned, explicitly authorized, or isolated lab environments.

Detection awareness: Assume commands, binaries, network calls, identity changes, and cloud or directory actions may be logged by endpoint tooling, audit frameworks, SIEM pipelines, proxy logs, DNS logs, auth logs, and platform telemetry.

Blue-team view: Treat every technique as a defender validation exercise too: note what artifacts it creates, what alerts or hunts could surface it, and what monitoring or hardening would prevent or contain it.

CTF/lab boundary: If a sandbox or CTF includes bypass-oriented exercises, keep them confined to that environment and translate the lesson into detection, prevention, and cleanup notes rather than real-world evasion guidance.

Master OW64 Grid — Harada Mandala Chart

Tip

How to read: The center goal is surrounded by 8 core pillars. Click any pillar to see its 8 action items in the dedicated file. Complete all 64 items to achieve the central goal. P0 is the pre-pillar for initial access, and exfiltration is integrated into the Linux and Windows full-chain workflows instead of living in a separate pillar.

🟣 P8 · Reporting 🔴 P1 · Linux 🟠 P2 · Windows/AD
📡 P7 · C2 Infra 🎯 Become a Red Team Operator 🌐 P3 · Web
P6 · EDR 🔵 P5 · Cloud 🟢 P4 · Networking
🚪 P0 · Initial Access (extended skills) 📤 Exfiltration · inside Linux + Windows/AD

Operational Overview

graph TB
    Goal((Red Team Operator))
    style Goal fill:#ff6600,stroke:#333,stroke-width:4px

    subgraph P1[Linux]
        L1[Enumeration & Phases]
        L2[SUID/SGID/Caps Exploit]
        L3[Cron & Service Abuse]
        L4[Kernel Exploit]
        L5[SSH Pivoting & Keys]
        L6[Container Escape]
        L7[Linux Persistence]
        L8[Full Linux Chain]
    end

    subgraph P2[Windows/AD]
        W1[System Enumeration]
        W2[Windows PrivEsc]
        W3[Credential Harvesting]
        W4[Windows Persistence]
        W5[AD Recon & Enum]
        W6[Kerberos Attacks]
        W7[NTLM Relay & Lateral]
        W8[ACL/ADCS/Domain Dom]
    end

    subgraph P3[Web]
        WB1[HTTP Recon & Phases]
        WB2[OWASP Top 10]
        WB3[Auth Attacks]
        WB4[API Hacking]
        WB5[SQL & Injection]
        WB6[Burp Suite Pro]
        WB7[File Upload & SSRF]
        WB8[Full Web Engagement]
    end

    subgraph P4[Network]
        N1[Post-Pivot Enum]
        N2[Quiet Port Scanning]
        N3[SOCKS w/ ligolo-ng and chisel]
        N4[Port Forwarding]
        N5[DNS Tunneling]
        N6[Infra Enumeration]
        N7[Full Pivot Chain]
    end

    subgraph P0[Initial Access]
        IA1[Recon and Portal Discovery]
        IA2[Password Spraying]
        IA3[Phishing and EvilGinx2]
        IA4[Public CVE Exploitation]
        IA5[Foothold Stabilization]
    end

    subgraph P5[Cloud]
        CL1[Cloud Identity]
        CL2[Cloud Enum & Recon]
        CL3[IAM PrivEsc]
        CL4[Token Theft & Abuse]
        CL5[IMDS Abuse]
        CL6[Azure AD Attacks]
        CL7[Serverless & Containers]
        CL8[Full Cloud Engagement]
    end

    subgraph P6[EDR]
        E1[AV Evasion]
        E2[AMSI Bypass]
        E3[Process Injection]
        E4[ETW & Unhooking]
        E5[Syscall Evasion]
        E6[Sleep Obfusc & Stack]
        E7[EDR Bypass Method]
        E8[LOLBins & BYOVD]
    end

    subgraph P7[C2]
        C1[Choose Framework]
        C2[Beacon Profiles]
        C3[Redirectors & Jump Infra]
        C4[Operate Sliver]
        C5[Operate Cobalt Strike]
        C6[Operate Mythic]
        C7[Advanced Channels]
        C8[BOF & Beacon Dev]
        C9[Full C2 Deployment]
    end

    subgraph P8[Reporting]
        R1[Finding Documentation]
        R2[Executive Summary]
        R3[Technical Report]
        R4[Remediation Mapping]
        R5[Attack Path Docs]
        R6[Public Writeup]
        R7[Tool Repo Curation]
        R8[Full Portfolio Dev]
    end

    P0 --> Goal
    Goal --- P1
    Goal --- P2
    Goal --- P3
    Goal --- P4
    Goal --- P5
    Goal --- P6
    Goal --- P7
    Goal --- P8

Foundational Cheatsheets

Execution Model

Daily Micro-Practice (30–60 min total):

Rotating Deep Pillar (60–120 min — pick one per day):

Day Focus
Monday C2 Infrastructure
Tuesday EDR Bypass / Evasion
Wednesday Networking & Pivoting
Thursday Cloud
Friday Full Attack Path Lab
Saturday Web & API
Sunday Review + Documentation

Progress Tracking

Level Criteria
[Beginner] Can perform the technique with reference material / walkthrough
[Intermediate] Can perform independently in a lab environment
[Advanced] Can adapt and apply in novel scenarios under time pressure
[Operator] Can chain techniques into complete attack paths on real engagements

Prerequisites

Before starting this series, ensure you are comfortable with the concepts in the Recon series:

# Pillar File Skill Range MITRE Focus Action Items
0 Initial Access (pre-pillar) 0.4_Initial_Access Intermediate → Operator Initial Access (TA0001) External recon, password spray, GoPhish, EvilGinx2 MFA bypass, public CVE exploitation, foothold stabilization
1 Linux 1_Linux Beginner → Operator Persistence, PrivEsc Enumeration (8 phases incl. Phase 7.5), SUID/SGID, Cron Abuse, Kernel Exploit, SSH Pivoting, Container Escape, Persistence, Full Chain + Linux exfiltration
2 Windows/AD 2_Windows_AD Beginner → Operator Lateral Movement, Credential Access Enumeration (8 phases incl. Phase 7.5), PrivEsc (incl. WES-NG/HiveNightmare), Cred Harvest, Persistence, AD Recon (9 phases), Kerberos, NTLM Relay, ACL/ADCS/RBCD/LAPS/GPP, Full Chain + Windows exfiltration
3 Web 3_Web Beginner → Operator Initial Access, Injection HTTP Recon (4 phases incl. Phase 0), OWASP Top 10, Auth Attacks, API Hacking, SQL Injection, Burp Suite Pro, File Upload/SSRF, Full Engagement
4 Networking 4_Networking Beginner → Operator C2, Discovery, Pivoting Post-Pivot Enum, Port Scanning (4 phases incl. Phase 4), ligolo-ng/chisel/rpivot, Port Forwarding, DNS Tunneling, Infra Enum, Full Pivot Chain
5 Cloud 5_Cloud Beginner → Operator Initial Access, Persistence Cloud Identity, Enum/Recon, IAM PrivEsc, Token Theft, IMDS Abuse, Azure AD Attacks, Serverless/Containers, Full Cloud Engagement
6 EDR 6_EDR Beginner → Operator Defense Evasion AV Evasion, AMSI Bypass, Process Injection, ETW/Unhooking, Syscall Evasion, Sleep Obfusc/Stack Spoof, EDR Bypass Method, LOLBins/BYOVD
7 C2 Operations 7_C2 Beginner → Operator Command and Control Framework selection, beacon creation, redirectors/jump infra, Sliver, Cobalt Strike, Mythic, advanced channels, BOF development, full deployment
8 Reporting 8_Reporting Beginner → Operator Operational Excellence Finding Documentation (3 phases), Exec Summary, Technical Report, Remediation Mapping, Attack Path Docs, Public Writeup, Tool Repo, Full Portfolio

Pillar Content Index

Quick-reference breakdown of what's inside each pillar file.

🔴 P1 — Linux (1_Linux.md)

Action Item Skill Key Phases
1 — System & Environment Enumeration [Beginner] Phase 1–7 + Phase 7.5 (Unknown Process/Service ID)
2 — SUID/SGID/Capabilities Exploitation [Beginner]
3 — Cron Job & Service Abuse [Intermediate]
4 — Kernel Exploit Identification & Execution [Intermediate]
5 — SSH Pivoting & Key Harvesting [Intermediate]
6 — Container Escape Techniques [Advanced]
7 — Linux Persistence Mechanisms [Advanced]
8 — Full Linux Attack Chain [Operator]

Linux Operator Field Guide: 1.1a Part 1 — OPSEC, process masquerading, PrivEsc · 1.1b Part 2 — Looting, Persistence, Cleanup, Sliver C2, NFS exploitation

Linux C2 Field Guide: 7.9a Sliver C2 Linux — install, generation, in-memory delivery, listeners (Sliver operator docs → P7)

macOS Post-Exploitation: 1.3_macOS_Post_Exploitation — SIP/TCC, Keychain, browser creds, cloud tokens, LaunchAgent persistence, Poseidon C2, dylib hijacking

🟠 P2 — Windows/AD (2_Windows_AD.md)

Action Item Skill Key Phases
1 — System & Environment Enumeration [Beginner] Phase 1–7 + Phase 7.5 (Unknown Service/Binary ID)
2 — Windows Privilege Escalation [Beginner/Intermediate]
3 — Windows Credential Harvesting [Intermediate]
4 — Windows Persistence [Intermediate]
5 — Windows/AD Recon & Enumeration [Intermediate] Phase 0–8 (DNS → BloodHound)
6 — Kerberos Attacks [Intermediate]
7 — NTLM Relay & Lateral Movement [Advanced]
8 — ACL Abuse, ADCS & Domain Dominance [Advanced]

🌐 P3 — Web (3_Web.md)

Action Item Skill Key Phases
1 — HTTP Fundamentals & Web Recon [Beginner] Phase 0 (Unknown App First Contact), Phase 1–3
2 — OWASP Top 10 Exploitation [Beginner]
3 — Authentication Attacks [Beginner]
4 — API Hacking [Intermediate]
5 — SQL Injection & Injection Attacks [Intermediate]
6 — Burp Suite Pro Workflow [Intermediate]
7 — File Upload & SSRF Chains [Advanced]
8 — Full Web Engagement [Operator]

🟢 P4 — Networking (4_Networking.md)

Action Item Skill Key Phases
1 — Network Enumeration Post-Pivot [Beginner] Phase 1–3 (Host Context → Service Discovery)
2 — Quiet Port Scanning [Intermediate] Phase 1–3 + Phase 4 (Unknown Port/Protocol ID)
3 — SOCKS Proxy with ligolo-ng, chisel & rpivot [Intermediate]
4 — Port Forwarding Deep Dive [Intermediate]
5 — DNS Tunneling [Intermediate]
6 — Network Infrastructure Enumeration [Intermediate] Phase 1–3 (CDP/LLDP → SNMP → Routing)
7 — Full Network Pivot Chain [Operator]
VPN Tunneling & WireGuard Pivots [Advanced]
VLAN Hopping & Segmentation Bypass [Advanced]

Pivoting & Tunneling Deep Dive: 4.1_Pivoting_and_Tunneling — Tool decision tree, ligolo-ng TUN setup, chisel, rpivot, SSH tunnels, proxychains, double pivot, OPSEC cleanup

🔵 P5 — Cloud (5_Cloud.md)

Action Item Skill Key Phases
1 — Cloud Identity Fundamentals [Beginner] Phase 1–2 (Tenant Context, Identity Recon)
2 — Cloud Enumeration & Recon [Beginner]
3 — IAM Privilege Escalation [Intermediate]
4 — Token Theft & Abuse [Intermediate]
5 — IMDS Abuse [Intermediate]
6 — Azure AD / Entra ID Attack Paths [Advanced]
7 — Serverless & Container Attacks [Advanced]
8 — Full Cloud Engagement [Operator]

⚫ P6 — EDR (6_EDR.md)

Action Item Skill Key Phases
1 — AV Evasion Fundamentals [Beginner]
2 — AMSI Bypass Techniques [Beginner]
3 — Process Injection Techniques [Intermediate]
4 — ETW Patching & Unhooking [Intermediate]
5 — Syscall-Based Evasion [Advanced] 6.2 Syscall Evasion Deep Dive
6 — Sleep Obfuscation & Stack Spoofing [Advanced] 6.3 Sleep Stack Evasion
7 — EDR Bypass Methodology [Advanced] 6.4 CS Process Evasion
8 — LOLBins, BYOVD & WDAC Bypass [Advanced] 6.5 ASR WDAC Bypass

EDR Deep Dives:

📡 P7 — C2 Infrastructure (7_C2.md)

Action Item Skill Key Phases
1 — Choose a C2 Framework [Beginner] Sliver vs Cobalt Strike vs Mythic
2 — Create a Beacon Profile [Beginner] Build guardrails, transport choice, validation
3 — Build Redirector & Jump Infrastructure [Intermediate] 7.11 C2 Jump Server Infrastructure, 7.2 C2 infra
4 — Operate Sliver [Intermediate] 7.9a Sliver C2 Linux, 7.10 Sliver C2 Windows
5 — Operate Cobalt Strike [Intermediate] 7.13 Cobalt Strike Setup Infra
6 — Operate Mythic [Intermediate] 7.4 Mythic C2 Operator Guide
7 — Traffic Shaping & Advanced Channels [Advanced] 7.6 Sliver HTTP C2 Profiles, 7.7 Advanced C2 Techniques
8 — Extend C2 Capabilities [Advanced] 7.12 Rust Beacon Development
9 — Full Infrastructure Deployment [Operator] 7.5 C2 Infrastructure Walkthrough

C2 Deep Dives by Function:

Cloud Deep Dives:

Lab & Validation:

🟣 P8 — Reporting (8_Reporting.md)

Action Item Skill Key Phases
1 — Finding Documentation [Beginner] Phase 1–3 (Evidence → Triage → Write-Up)
2 — Executive Summary Writing [Beginner]
3 — Technical Report Writing [Intermediate]
4 — Remediation Framework Mapping [Intermediate]
5 — Attack Path Documentation [Intermediate]
6 — Public Writeup Creation [Advanced]
7 — Tool Repository Curation [Advanced]
8 — Full Portfolio Development [Operator]

🚪 P0 — Initial Access (0.4_Initial_Access.md) (pre-pillar)

Section Skill Coverage
External Recon & Portal Discovery [Beginner] OWA, O365, VPN fingerprinting, email format OSINT
MFA Posture Assessment [Intermediate] Legacy auth, MFASweep, decision table
Password Spraying [Intermediate] SprayingToolkit, o365spray, TREVORspray, Citrix/PAN-OS
Phishing Infrastructure (GoPhish) [Intermediate] Sending profile, landing page, template, campaign
MFA Bypass (EvilGinx2) [Advanced] Phishlet setup, lure, session cookie capture, replay
Public CVE Exploitation [Advanced] ProxyShell, Citrix CVE-2023-3519, Fortinet, VMware, nuclei
Foothold Stabilization [Operator] Web shell → C2 beacon via download cradle

Portfolio Reminder

Note

Publish one technical artifact every 4–6 weeks.
Examples: red team writeup, offensive tool repo, detection bypass research, attack path diagram, blog post.
Companies like Mandiant, CrowdStrike, and Microsoft hire people who demonstrate thinking, not just certifications.


Red Team 101 — Operational Doctrine

BLUF: Technical skill is table stakes. What separates an operator from a hobbyist is how they plan, document, communicate, and manage risk throughout an engagement.


Pre-Ops: Planning & Authorization

Nothing executes without paper. If you don't have written authorization you are committing a crime, not running a red team engagement.

Required Before Day 1:

Document Purpose
Statement of Work (SoW) Defines scope, deliverables, timeline, cost
Rules of Engagement (RoE) What you CAN do — techniques, hours, escalation process
Authorization Letter Legal protection if challenged by law enforcement
Emergency Contact List Who to call 24/7 if something breaks

RoE Must Explicitly Address:

Warning

Stay in your lane. If you find something that requires going outside agreed scope, stop and call the client. Do not exploit it. Document it. Ask.


Op Plan

Sections:

  1. Objective — What does success look like? (e.g., "Achieve DA without triggering a SOC alert")
  2. Target Profile — Known intel: tech stack, AV/EDR, network segmentation, users
  3. Phasing — Recon → Initial Access → Post-Ex → Lateral Movement → Objectives → Reporting
  4. TTP Selection — Specific techniques planned per phase, mapped to MITRE ATT&CK
  5. Contingency — What happens if you get caught? How do you re-establish access?
  6. Exit Criteria — When do you stop?

Infrastructure

Standard Red Team Infra Stack:

Component Purpose Examples
Jump Server / VPS Operator access point, external-facing DigitalOcean, Vultr, AWS EC2, Residential Proxy
C2 Server Beacon callbacks, session management Cobalt Strike, Sliver, Mythic
Redirectors Traffic filtering, attribution protection Nginx, Apache, Cloudflare
Operator Workstation Local machine for tooling and sessions Kali, ParrotOS, hardened VM
Training / Testing VMs Offline tool testing before deployment Local VirtualBox/VMware lab
Collaboration Team comms, task tracking Slack, Mattermost, Obsidian

Infrastructure Rules:


Workstation Hardening (Assessment Laptop)

Your laptop is the most sensitive device in the engagement. If it's compromised or stolen, the client's network is compromised too.

OS & Build:

How to:

# Enable LUKS full-disk encryption during OS install (Kali/Ubuntu installer — check "Encrypt" option)
# Or encrypt an existing partition post-install:
cryptsetup luksFormat /dev/sdX
cryptsetup luksOpen /dev/sdX encrypted_vol

# Auto-lock (GNOME)
gsettings set org.gnome.desktop.session idle-delay 300
gsettings set org.gnome.desktop.screensaver lock-enabled true

# Patch before engagement
sudo apt update && sudo apt full-upgrade -y

# Disable Bluetooth
sudo systemctl disable bluetooth --now

# Disable USB auto-mount (GNOME)
gsettings set org.gnome.desktop.media-handling automount false

Compartmentalization:

How to:

# Create a new KVM/QEMU VM for the engagement (or use VirtualBox)
virt-manager  # GUI — create new VM, allocate disk, take snapshot before connecting

# VirtualBox snapshot before connecting to client
VBoxManage snapshot "EngagementVM" take "pre-client-connect" --description "Clean state"

# Verify VPN is up on host BEFORE starting VM
curl ifconfig.me  # confirm you're hitting VPN exit IP, not home ISP

Network Discipline:

How to:

# Verify no split tunnel — all traffic should exit VPN
ip route show   # default route should point to tun0/wg0, not eth0/wlan0

# Check for DNS leakage
cat /etc/resolv.conf          # should show VPN DNS, not home router
dig +short myip.opendns.com @resolver1.opendns.com   # verify exit IP

# Enable DNS over HTTPS (systemd-resolved)
sudo nano /etc/systemd/resolved.conf
# Set: DNS=1.1.1.1  DNSOverTLS=yes
sudo systemctl restart systemd-resolved

Credential & Key Hygiene:

How to:

# Generate a per-engagement SSH keypair
ssh-keygen -t ed25519 -C "eng-clientname-2026" -f ~/.ssh/id_eng_clientname

# Suppress shell history for the session
unset HISTFILE
# Or prefix sensitive commands with a space (requires HISTCONTROL=ignorespace in .bashrc)
export HISTCONTROL=ignorespace

# Destroy keypair at engagement close
shred -u ~/.ssh/id_eng_clientname ~/.ssh/id_eng_clientname.pub

# Wipe known_hosts entries for client hosts
ssh-keygen -R <client-ip>

Physical Security:


Risk Management

Risk-Adverse Mindset:

Attack vs. Defend Mindset:

Attack Mindset Defend Mindset Red Team Balance
"How do I get in?" "How do I detect this?" Think both simultaneously
Maximize access Minimize noise Quiet access, loud findings
Exploit everything Protect everything Exploit only what's in scope
Win Survive Complete the objective, leave cleanly

Knowledge Management

What to Capture:

Repository & Data Transfer Plan:

Caution

Never store client loot on public cloud drives, unencrypted personal devices, or any system outside the defined engagement infrastructure.


Op Notes

Op notes are your real-time log. They are the source of truth for the final report and any deconfliction.

Every Entry Must Include:

[TIMESTAMP UTC]  ACTION
Command:   <exact command run>
Target:    <IP / hostname / URL>
Result:    <exact output or summary>
Artifacts: <file dropped, service created, key used, etc.>
Screenshot: <filename or link>
Note:      <why you did this / what you expected vs got>

Op Note Discipline:


Analyst Journal (Narrative Log)

Separate from op notes — a narrative account written in past tense. This is the raw material for the attack narrative in the final report.

Journal Format:

[DATE TIME UTC] — Narrative sentence describing what happened and why.

Example:
[2026-03-08 14:32 UTC] — Performed Kerberoasting against all SPN accounts.
Identified svc_sql with RC4 encryption. Hash cracked in 4 minutes via rockyou.txt.
Used resulting credential to authenticate to SQL01 as a domain user.

Journal vs Op Notes:

Attribute Op Notes Analyst Journal
Format Structured fields Prose narrative
Timing Real-time End of session / phase
Audience Yourself, teammates Report reader
Detail level Maximum Summarized

TTPs

Document every TTP used. This drives the MITRE ATT&CK mapping in the final report and helps the blue team build detections.

TTP Log Format:

Phase MITRE ID Technique Tool Used Target Result
Recon T1595 Active Scanning nmap 10.10.10.0/24 12 live hosts
Cred Access T1558.003 Kerberoasting Rubeus domain.local 3 hashes obtained
Lateral Move T1021.002 SMB Exec wmiexec.py 10.10.10.5 Shell as svc_sql

TTP Discipline:


Reporting Cadence

Report Frequency Audience Content
Daily Sitrep End of each op day Client POC Progress, systems accessed, blockers, next steps
Mishap Report Immediately on incident Client POC + Management What happened, impact, containment, RCA
Deficiency Report As discovered Client technical lead Critical finding needing immediate attention
Final Report End of engagement All stakeholders Executive summary, all findings, attack narrative, TTP log, remediation

Daily Sitrep Template:

Date:             [DATE]
Operator:         [NAME]
Objective Today:  [WHAT YOU PLANNED]
Accomplished:     [WHAT YOU DID]
Systems Accessed: [IP / HOSTNAME LIST]
Findings:         [NEW FINDINGS SUMMARY]
Blockers:         [ANYTHING STOPPING PROGRESS]
Plan Tomorrow:    [NEXT STEPS]
Risk Items:       [ANYTHING NEEDING CLIENT ATTENTION]

Mishap Report Triggers — Stop and report immediately if you:


Post-Engagement Debrief

Cleanup Checklist:

Debrief Meeting Agenda:

  1. Walk the client through the attack narrative — show the path, not just the findings
  2. Demonstrate key findings with live reproduction (if safe)
  3. Map each finding to a defensive control that would have blocked or detected it
  4. Discuss detection gaps identified from the TTP log
  5. Agree on a remediation timeline