HTB Beginner Guide — Hands-On Connecting to HTB & Solving Issues | By: CyberAlp0

Beginner Guide to solving HackTheBox Machines | By:@cyberalp0

Starting your journey on Hack The Box can feel overwhelming, especially for newcomers. The process of connecting to the VPN, spawning a machine, enumerating it, and successfully hacking it can be a lot to handle.

That’s why I am introducing a series of blogs and write-ups that will give you a hands-on beginning with HTB labs and how to build a good mindset for solving the labs at different levels. starting with the “Starting Point” levels.

Starting Point Labs are designed to be a beginner-friendly experience, providing a linear series of machines with easy exploit paths, helping you understand how the platform works, connect with machines, and develop a foundational understanding of hacking.

Each Starting Point machine will be explained in a detailed writeup published in my profile, mentioning the solving walkthrough and concepts involved.

Also, you will find at the end of this blog a walkthrough into solving the most popular issues that you may encounter while connecting to the HTB VPN.

Step 1: Connecting to HTB Servers

To gain access to the machine, you will be prompted to be on the same network as the HTB Lab. Thus, you will navigate to the “Connect to HTB” section (on the top right of the window). Click on the starting point as shown in the below screenshot.

Connecting to HTB Servers Via VPN, in order to obtain the IP addresses of the starting point labs.

Once you click on “Connect to HTB”, Click on the “Starting Point” as shown in the below screenshot.

Connecting to the “Starting Point” labs.

Then, Connect to the “Starting Point” Labs using OpenVPN, as shown in the below screenshot.

Connecting to the “Starting Lab” labs using OpenVPN.

Once you click on the OpenVPN option, you will be redirected to another window that has lots of options. leave all options as it is and just click on “Download VPN”.

You shall find a file with an extension “.ovpn” downloaded in the Downloads Directory.

Downloading the .ovpn file in order to connect to the server of the starting point labs.

Step 2: Connecting Kali to the “Starting Point” Labs Servers

To connect to the HTB Starting Point Labs Servers. you shall write the following command on the terminal to successfully connect to the servers of “Starting Point Labs”.

Connecting to the servers of the Starting Point Labs through the command “openvpn”.

If you aren’t a root user, make sure you type sudo before the command.

Finally, You are now successfully connected to the HTB Starting Point Servers.

To make sure you are connected successfully, you shall see the “starting Point” button lighted with green on the top right corner of the window, as shown in the below screenshot.

You are now connected successfully to the “Starting Point Servers” to solve the machines.

Step 3: Spawn the machine and begin hacking!

Choose the machine you wish to solve and click on “SPAWN MACHINE” as shown in the below screenshot.

Fetching the IP of the Machine, you want to PWN.

You will find the IP address of the Machine shown in the screenshot below.

IP Address of “Three” Machine.

Bonus Section: Solving Connection Issues

Issue 1: TLS Error: TLS key negotiation failed to occur within 60 seconds | TLS handshake Failed

TLS Error: TLS key negoitiation filed to occur within 60 seconds

This is one of the most popular issues you may face while connecting to the starting point VPN. This error means that the TLS (Transport Layer Security) handshake process was not completed within the expected time frame which equals 60 seconds. This error happens due to many reasons, the most important of which are:

1. Network Connectivity Issues: Ensure that your internet connection is stable and that no firewalls or network restrictions are blocking the VPN traffic.
2. Incorrect Configuration: Double-check your OpenVPN configuration file (.ovpn) for any errors. Ensure that the server address, port, and certificate paths are correctly set.
3. Server Unavailability: The Hack The Box VPN server might be temporarily down or experiencing issues. Check the status on their official forums or Discord server.
4. Firewall or Antivirus Interference: Your local firewall or antivirus software may be blocking the OpenVPN connection. Try disabling them temporarily to see if it resolves the issue.
5. Outdated OpenVPN Version: Ensure that you are using the latest version of OpenVPN. An outdated client may have compatibility issues.
6. Multiple VPN Connections: If you have multiple VPN configurations or active connections, it can cause conflicts. Disconnect any other VPN clients before attempting to connect to Hack The Box.

Yet, You checked the above points and the issue still exists? Here is the solution

Once you download the .ovpn file from HTB, it will be saved by default in the /Downloads directory. Edit this file using a text editor like “vim”, and make sure to edit the following values

• Change “Proto udp” to “Proto tcp”
• change “remote {serverAddressHere} 1337” to “remote {serverAddressHere} 443”.

Changing the valuse of proto udp & the port of the remote server address.

• Change <tls-auth> to <tls-crypt>
• Change </tls-auth> to </tls-crypt>

changing the parameter of the <tls auth> to <tls crypt>.

Now, Begin solving the tasks of the machine till you find the machine flag.

You can check my Blogs/Write-ups, in which I explain step-by-step how you can start solving different machines on HTB in various stages.