Hackthebox Red Failure -

Before we fix the problem, we must diagnose the symptoms. A typical "Red failure" follows a predictable psychological arc.

When you see that red message during an exploit attempt, follow this checklist:

You fire up Nmap. You see ports 22 (SSH) and 80 (HTTP). You think, "An Easy box with only two ports? This will take ten minutes." You visit the website. It's a default Nginx page. You run gobuster, dirb, and ffuf. You find nothing. hackthebox red failure

Note: I interpret “Hack The Box — Red Failure” as an inquiry into the Red Team (offensive) track, failure modes encountered on Hack The Box labs/challenges (often labeled “red”/offensive), and broader lessons about offensive security practice and learning from failures. I’ll assume the audience is an intermediate-to-advanced practitioner interested in pedagogy, methodology, and operational security. If you meant a specific retired or named machine/challenge called “Red Failure,” tell me and I’ll tailor this to that exact target.

You likely forgot to check for log files. Inside Red, after you get the initial shell, there is a log file in /var/log/audit/ that explicitly tells you which commands are not allowed to run as root. If you had simply typed cat /var/log/audit/audit.log, you would have seen the race condition requirement immediately. Failure: You didn't read the logs. Red logs everything. Before we fix the problem, we must diagnose the symptoms

You finally get a shell as a low-privilege user (alex or similar). You run sudo -l. You see (ALL : ALL) NOPASSWD: /usr/bin/pip. "Wow," you think. "Easy. sudo pip install reverse shell."

Why you failed: The system is hardened. It has noexec on the temp directory. It has AppArmor enabled. A standard pip exploitation fails because you cannot write a malicious setup.py to disk due to permissions. You finally get a shell as a low-privilege

The Real Root Path (The "Red" specific trick): Red requires a Race Condition or a Library Hijack. Because you can run pip as root, but cannot write files, you must trick pip into loading a malicious library from a network share or from a directory you can write to (like /dev/shm or /run/user/1000).

The winning move:

# Create a malicious setup.py in /dev/shm
echo 'import os; os.system("chmod u+s /bin/bash")' > setup.py
# Create a fake package
mkdir /dev/shm/pwn
# Force pip to install the local directory as root
sudo pip install /dev/shm/pwn --no-cache-dir
# Then run: /bin/bash -p

If you didn't think to check sudo -l immediately upon gaining a shell, or if you assumed pip privilege escalation required internet connectivity (it doesn't), you failed.