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OSCP Prep Box 56 – Gaara – Proving Grounds Play

Posted on March 15, 2026March 15, 2026

Hi everyone

Today we are going to look for a Box called Gaara which is rated as easy in terms of difficulty. This machine has various phases: Recon, Enumeration, Exploitation and Privilege Escalation.

Box Type: Linux

Table of Contents
  • Recon & Enumeration
  • Exploitation
  • Privilege Escalation
  • Key Takeaways

Recon & Enumeration

Enumeration plays a very significant role in pen testing. The more properly you enumerate the more it will be easy to get a foothold on the target.

First, we will check whether target is reachable or not with ping command:

ping Target_IP

With ping command output we found that the target is reachable.

Now let’s move ahead and run the port scan for which we will be using Nmap a popular tool for port scanning and it will provide details of the various ports which are in Open state. The command for that will be:

nmap -sC -sV -O -oA nmap/initial 192.168.206.142

nmap -sC -sV -O -p- -oA nmap/full 192.168.206.142 -T4

I discovered these ports are open:

  • 22/tcp – SSH Service running OpenSSH 7.9p1 Debian 10+deb10u2 (protocol 2.0)
  • 80/tcp – HTTP Service running Apache httpd 2.4.38 ((Debian))
  • OS: Linux

Then I went ahead and checked the IP in the web browser and I found a wallpaper running:

I got the creds but no luck

Exploitation

I found the password from Hydra and used it log in to SSH

I found the local.txt flag

Privilege Escalation

Now it was a time for escalating the privileges.

The above image shows the proof.txt file.

Key Takeaways

  • Full port and service enumeration first — even simple services can reveal the entry point.
  • Hidden directories can expose useful clues — web enumeration should never be skipped.
  • Encoded strings or unusual data often hide credentials — always try decoding them.
  • Weak credentials remain a common foothold — once a username is known, access may follow quickly.
  • Always enumerate SUID binaries after gaining a shell — misconfigured ones can lead straight to root.
  • Privilege escalation is often about trusted binaries — if a powerful tool runs with SUID, it may give full control.

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