HackTheBox Dante Lab: A Comprehensive Review

The HackTheBox Dante lab is a highly demanding and rewarding challenge that will test your penetration testing skills to the limit. It is designed for experienced Red Team operators and is considered one of the good challenging exercises on the platform. Which has the set of 14 machines and 27 flags to take out.

This Lab come under the category of Penetration Tester Level I and tester’s need below exploitation experience to complete this lab successfully.

Enumeration
Exploit Development
Lateral Movement
Privilege Escalation
Web Application Attacks

Initial Reconnaissance and Foothold Establishment:

The Dante lab starts with a reconnaissance phase, where you must identify and map the network layout. This involves scanning for open ports, identifying running services, and gathering information about the target systems. The network is surprisingly vast, with multiple Active Directory domains and various security measures in place.

Gaining access to the network requires a combination of techniques, such as social engineering, password cracking, or exploiting vulnerabilities. The process is not straightforward and may require multiple attempts before successfully compromising a system.

Navigating the Complex Network:

Once you gain access, the true challenge begins. Dante’s network is a complex web of interconnected systems, making it difficult to navigate and understand the overall structure. To progress, you’ll need to carefully analyze network traffic and identify potential pivot points for lateral movement.

The network is fortified with robust security measures, including two-factor authentication, Just Enough Administration, and Windows Defender Application Control. These safeguards pose challenges in escalating privileges and accessing more sensitive systems.

Crucial Role of Lateral Movement and Privilege Escalation:

In Dante, the focus is heavily on moving laterally and escalating privileges. You’ll have to use different techniques to navigate between systems and attain higher levels of authority. This could mean exploiting vulnerabilities, employing social engineering tactics, or taking advantage of misconfigurations.

Privilege escalation in Dante requires exploiting multiple vulnerabilities to reach domain admin level. This requires a deep understanding of Active Directory and the skill to connect various attack vectors.

Lack of Clear Paths and Known Vulnerabilities:

One of the unique aspects of Dante is that it intentionally avoids relying on known vulnerabilities (CVEs). This forces you to think creatively and apply your knowledge of various attack techniques to find new and innovative ways to compromise the system.

The lack of clear paths also makes Dante a more challenging lab. There may not be a single obvious way to solve a challenge, and you may need to explore multiple avenues before you find the correct solution.

Let us Deep dive,

My methodology involved utilizing a multifaceted strategy that combined

1. Traditional ssh sessions, by utilizing various useful SSH features.
2. Using an HTTP to SOCKS proxy lets Burp guide traffic to the Dante network and the Internet selectively. This is crucial for sites in Dante that may load poorly without access to Internet-based resources on some pages, and Burp’s regular SOCKS proxy is an all-or-nothing option
3. To enable regular tools to function through the dynamic SOCKS proxies generated by SSH, utilize ProxyChains4, a proxy chaining tool for Linux and Unix-like operating systems.
4. Leverage Meterpreter payloads on pivot hosts to utilize Metasploit’s routing functionalities, enabling seamless communication and control across the Dante network.

I ensured secure authentication for SSH by using keys. If a user lacked a key on a system, I added my own (specifically generated for Dante). Additionally, I configured the host entry in my SSH config file for added convenience. This streamlined SSH for various tasks, such as swift file transfers to and from the host. It also facilitated chaining multiple SSH connections together using the ProxyCommand option.

To establish a SOCKS proxy on port 1080 on my local host, I employed the DynamicForward option. Traffic directed through this proxy would subsequently be routed via the remote host. This technique proved particularly useful for forwarding traffic from my local host to the network directly connected to the remote SSH host. For each SSH configuration entry designated as a routing point for additional traffic, I included one of these DynamicForward options (each with a unique port).

I would utilize these SOCKS proxies to route traffic from Burp through the aforementioned HTTP-to-SOCKS proxy. Additionally, I created individual ProxyChains4 configuration files for each SOCKS proxy port. These configuration files were employed when running ProxyChains4 to direct traffic to the appropriate networks, as here how it looks like:

proxychains4 -q -f proxychains_1080.conf <command> <options>

In this scenario, you can also use SOCKSIFY to do the same operation by,

socksify -i -D 1080 <command> <options>

A helpful suggestion when using proxychains is to make sure that if you’re running an interpreted program, such as a Python script, it’s advisable to explicitly mention the Python binary before the script, even if the script begins with a hash bang, for example:

proxychains4 -q -f proxychains_1080.conf python your_script.py

Omitting explicit reference the script interpreter, there’s a chance that the traffic generated by the script may not be routed through the proxy as intended, leading to a failure in network connection.

The ProxyCommand option points to another proxy configuration entry in the same file, labeled “dante-host1.” This directs your SSH client to initially establish a connection to “dante-host1” and then tunnel the connection to “dante-host2” through that session. Essentially, this automatically guides you through “dante-host1” to reach “dante-host2.” You can also link these entries, creating a similar setup for “dante-host3” with a ProxyCommand entry referring to “dante-host2,” enabling the connection to pass through “host1” and “host2” to ultimately reach “host3.” This proves highly convenient when you need to SSH into a host that requires multiple hops for access.

Create a local port forward from port 8888 to the remote host and port 172.16.1.1:8000 in the current session

ssh> -L 8888:172.16.1.1:8000

Metasploit was a key tool in Dante, I frequently relied on its routing options to pivot strategically. By deploying Meterpreter payloads on specific hosts and adjusting the Metasploit routing table with the ‘route’ command, I could seamlessly route traffic to the 172.16.2.0/24 network through the Meterpreter agent on session 2, effectively connecting to targets with their respective IP addresses..

route add 172.16.2.0 255.255.255.0 2

My recommended approach of employing SSH with keys for connecting to compromised hosts, you can employ a useful trick with Metasploit. Utilize the “auxiliary/scanner/ssh/ssh_login_pubkey” module to obtain a shell session on those hosts in Metasploit. For instance, to connect to the host 10.10.10.10 as the user root with the key ~/.ssh/id_rsa_dante, follow these steps:

use auxiliary/scanner/ssh/ssh_login_pubkey
set USERNAME root
set RHOSTS 10.10.10.10
set KEY_PATH ~/.ssh/id_rsa_dante
exploit

Once you’ve successfully opened your session, you can enhance it by upgrading to Meterpreter, enabling routing capabilities using the ‘upgrade’ option. To upgrade session 1, execute a command similar to the following, initiating the Meterpreter session to that host with the next available session number:

sessions -u 1

Metasploit’s SOCKS proxy module (auxiliary/server/socks_proxy) provides an alternative method for forwarding traffic from external tools, similar to the SSH proxying approach. This method also utilizes Metasploit’s routing capabilities, enabling you to direct attack traffic via proxychains to any system accessible by Metasploit. While I primarily relied on SSH servers for traffic forwarding in DANTE, the SOCKS proxy module proves valuable in scenarios where SSH servers are unavailable. This approach offers the advantage of directing traffic to multiple network subnets through a single SOCKS port, as long as Metasploit can communicate with those segments via its routing through Meterpreter agents.

A Rewarding Challenge for Experienced Penetration Testers:

Dante is not a lab for the faint of heart. It is designed for experienced penetration testers with a strong understanding of Active Directory and security systems. The lab demands careful planning, thorough documentation, and a persistent mindset to overcome its numerous obstacles.

Despite its difficulty, Dante offers a valuable learning experience that will enhance your red teaming skills. The lab forces you to think outside the box and apply a wide range of techniques to achieve your objectives. If you are up for the challenge, Dante is a rewarding and unforgettable journey into the world of advanced penetration testing.