HackTheBox Endgames - Complete Walkthroughs

Multi-machine, multi-stage scenarios simulating real penetration testing engagements. Each endgame contains multiple flags across an interconnected network.

1. P.O.O. (Professional Offensive Operations)

Difficulty: Easy-Medium Hosts: 2 Windows Flags: 5

Overview

The first Endgame released by HTB. Two Windows hosts presented behind a single public-facing IP. Focuses on web enumeration, MSSQL exploitation, and linked server abuse.

Attack Chain

  1. Recon: Discover DS_STORE files and IIS short filenames (8.3 naming) to enumerate hidden paths
  2. Credential Discovery: Find MSSQL database connection string through tricky file enumeration
  3. MSSQL Exploitation: Connect to MSSQL instance with discovered credentials
  4. Linked Server Abuse: Exploit trust relationships between MSSQL linked servers to escalate access
  5. Code Execution: Abuse linked server trust to achieve command execution on the second host

Key Techniques

  • DS_STORE file enumeration
  • IIS 8.3 short filename brute-forcing
  • MSSQL enumeration (roles, grants, proxy accounts)
  • MSSQL linked server exploitation
  • Trust abuse between database servers

Writeup Resources

2. Xen

Difficulty: Medium-Hard Hosts: 6 (3 Windows workstations, 1 Netscaler/FreeBSD, 1 Citrix Windows, 1 Domain Controller) Flags: 5+

Overview

Test enumeration, breakout, lateral movement, and privilege escalation within a small Active Directory environment behind a Citrix virtual desktop.

Attack Chain

  1. Phishing: Social engineer/phish credentials from users in the Sales department
  2. Citrix Breakout: Use phished credentials to access Citrix VDI environment, then escape the restricted desktop
  3. Workstation Compromise: Privilege escalation on 3 end-user Windows computers
  4. Lateral Movement: Move through the network using harvested credentials
  5. Domain Compromise: Kerberoasting, credential extraction, DC takeover

Key Techniques

  • Social engineering / credential phishing
  • Citrix virtual desktop breakout
  • Windows local privilege escalation
  • Kerberoasting
  • Active Directory enumeration and exploitation
  • Domain Controller compromise

Writeup Resources

3. Hades

Difficulty: Hard Hosts: Multiple (small AD enterprise network) Flags: 5+

Overview

Put your Active Directory enumeration and exploitation, lateral movement, and privilege escalation skills to the test within a small enterprise network. The goal is to gain a foothold, escalate privileges, and ultimately compromise the domain.

Attack Chain

  1. Chasm (Initial Access): Enumerate external services, find entry point
  2. Guardian: AS-REP Roasting to obtain crackable hashes
  3. Lateral Movement: Exploit Printer Bug from Linux, decrypt DPAPI secrets
  4. Delegation Abuse: Kerberos Resource-Based Constrained Delegation (RBCD)
  5. DNS Spoofing: Spoof Active Directory-Integrated DNS for further access
  6. Domain Compromise: Full domain takeover

Key Techniques

  • AS-REP Roasting
  • Printer Bug exploitation (from Linux)
  • DPAPI secret decryption
  • Kerberos Resource-Based Constrained Delegation (RBCD)
  • Active Directory-Integrated DNS spoofing
  • Multi-stage lateral movement

Writeup Resources

4. RPG

Difficulty: Hard Hosts: Multiple Flags: 6

Overview

A challenging multi-machine scenario focused on Linux exploitation, network pivoting, and advanced techniques.

Flag Stages

  1. “Would You Like to Play a Game?” - Initial access
  2. “Sword and Mind” - Enumeration and exploitation
  3. “One’s Act, One’s Profit” - Lateral movement
  4. “The Source of Power” - Privilege escalation
  5. “Wake From Death and Turn to Life” - Advanced exploitation
  6. “Collapse of the Empire” - Final domain/network compromise

Key Techniques

  • Multi-machine network pivoting
  • Linux service exploitation
  • Advanced enumeration
  • Chained exploitation across hosts
  • Final domain compromise

Writeup Resources

5. Ascension

Difficulty: Hard Hosts: Multiple Flags: 7

Overview

An advanced endgame involving network enumeration, web application attacks, Active Directory hacking, and Windows privilege escalation.

Flag Stages

  1. Takeoff - Database enumeration (roles, grants, proxy accounts)
  2. Intercept - Capturing credentials/traffic
  3. Contrails - Lateral movement
  4. Wingman - Privilege escalation
  5. Corridor - Pivoting
  6. Upgrade - Advanced exploitation
  7. Maverick - Final compromise

Key Techniques

  • Blind SQL injection
  • MSSQL exploitation and agent jobs
  • MSSQL proxy abuse
  • Network pivoting
  • Resource-Based Constrained Delegation (RBCD)
  • Multi-stage Active Directory attacks

Writeup Resources

Endgame Progression Path 

P.O.O. (Beginner) --> Xen (Intermediate) --> Hades (Advanced) --> RPG (Advanced) --> Ascension (Advanced)
Endgame Focus Prerequisite Skills
P.O.O. MSSQL, Web Enum Basic web, SQL knowledge
Xen Citrix, AD Basics AD fundamentals, social engineering
Hades AD Advanced Kerberos, DPAPI, delegation attacks
RPG Linux Networks Linux exploitation, pivoting
Ascension Full-spectrum AD SQLi, MSSQL, RBCD, pivoting