Hackfail.htb
Use wfuzz or ffuf to fuzz the Host header. The box often serves entirely different virtual hosts based on subdomains like dev.hackfail.htb , admin.hackfail.htb , or vpn.hackfail.htb .
The journey begins by adding the target IP to your local /etc/hosts file as hackfail.htb . A comprehensive Nmap scan is the standard starting point to identify open ports and running services. Custom Content - Hack The Box Help Center
Let’s break down what hackfail.htb represents, the origin of its cryptic name, its technical hurdles, and why failing at this box might be the best learning experience you never knew you needed. hackfail.htb
The initial login page is susceptible to a Boolean-based blind SQL injection. We can test this by using the admin username and a payload like admin' AND '1'='1 in the password field. The goal here is not to extract data immediately, but to understand the database's structure. By carefully crafting queries, we can extract sensitive information, one character at a time. For a machine like Falafel, a standard tool like sqlmap is often too noisy. Instead, a custom Python script is usually written to automate the process of extracting the password hash for the admin user. This manual approach is excellent for learning the mechanics of blind SQL injection.
The real fail is in /root/fail_log . You can't read it. But you notice fail_trap calls cat /root/fail_log without sanitizing $PATH . You export PATH=/tmp:$PATH , create a fake cat that copies /root/fail_log . Run fail_trap — bingo. The log contains the root password hash. Use wfuzz or ffuf to fuzz the Host header
"data": "Ä\x00\xFF"
If the machine has a vulnerable version of pkexec (version below 0.105), it can be exploited using the well-known (PwnKit) vulnerability, allowing an attacker with local access to execute arbitrary commands as root. A comprehensive Nmap scan is the standard starting
As I continued to explore the box, I stumbled upon a misconfigured sudoers file. This configuration allowed me to execute a specific command with elevated privileges, paving the way for a smooth privilege escalation.
: While less common on modern HTB machines, always verify the kernel version for known vulnerabilities if other paths are exhausted. Summary Checklist Focus Areas Recon Nmap, directory busting (Gobuster/ffuf), vhost discovery. Web Logic flaws, session hijacking, or .git extraction. User Internal service exploitation or credential reuse. Root Sudo rights, SUID bits, or misconfigured system services. If you'd like to dive deeper, let me know: Which phase are you currently stuck on?
This is the "Fail" in hackfail . It is not a failure of skill; it is a failure of process. Seasoned penetration testers know that 80% of "hacking" is meticulous configuration. The hackfail.htb moment forces you to stop, check your tools, and verify Layer 3 connectivity before moving to Layer 7.
The naming convention is where things get interesting. Why would a security challenge be named "hackfail"?
