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Anonymous

OSCP Prep Box 21 – Anonymous – TryHackMe

Posted on July 29, 2025August 30, 2025

Hi everyone

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

This room was released by Nameless0ne. You can find the link here for this room.

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

This room includes various tasks that needs to be completed to solve the entire CTF.

BOX Questions

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

The ping was disabled on this machine so I directly initiated the nmap scans.

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 10.10.41.184 -Pn

Now let’s also execute the full scan:

nmap -sC -sV -O -p- -oA nmap/full 10.10.41.184 -Pn -T4

I executed the UDP scan also but it was taking long time so I stopped it:

We discovered these ports are open:

  • Port 21: an ftp service running vsftpd 2.0.8 or later with Anonymous FTP login allowed (FTP code 230) with rwx permissions for all.
  • Port 22: an ssh service running OpenSSH 7.6p1 Ubuntu 4ubuntu0.3 (Ubuntu Linux; protocol 2.0)
  • Port 139: netbios service running Samba smbd 3.X – 4.X (workgroup: WORKGROUP)
  • Port 445 :netbios service running Samba smbd 4.7.6-Ubuntu (workgroup: WORKGROUP)
  • Linux as the operating system.

Recon & Enumeration

Let’s move ahead with the FTP Anonymous login:

After successfully logging in to the ftp we found there is a directory with name scripts which has rwx permissions for all users and includes the files like clean.sh . removed)_files.log and to_do.txt and I quickly transferred that directory to my machine:

It was the time to check for the contents of all the three files inside the scripts directory. I found a message that talks about a good security practice to disable the anonymous logins:

Inside the removed_files.log nothing was there.

So the last one was clean.sh which was a bash script which was running a cleanup script:

Exploitation

So what I did basically is modified the script with a one liner reverse shell and started a netcat listener:

So with the one liner I was able to get a reverse shell connection:

I found certain files and offcourse the user.txt file, also I found 2 images with jpg and jpeg extensions inside the pics directory.

Privilege Escalation

Then it was time for privilege escalation. So I quickly fired a command to find the files with the SUID bit set and to list their details ignoring the errors with the following command:

find / -type f -perm -04000 -ls 2>/dev/null

I saw a tons of files but what caught my attention was /usr/bin/env which is a utility for running commands with a modified environment:

The shell was so unstable that I need to again pop up shell multiple times with different port numbers. So moving ahead I executed the following command to run bash in privileged mode which provided me the root access and I was able to get the root.txt:

/usr/bin/env /bin/bash -p

The above image shows that we got the root flag.

Key Takeaways

  • Always disable anonymous logins.
  • If one tool doesn’t give results try various switches as well as other tools.
  • Make sure that proper set of permissions are implemented for the files especially for the scripts.

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