Introduction
BackTrack Five, a once-prominent penetration testing distribution, holds a special place in the history of cybersecurity. While it has been superseded by more modern and secure distributions, such as Kali Linux, some users may still find value in exploring BackTrack Five for specific educational purposes, for familiarity with older tools, or for following legacy tutorials.
It is crucial to understand that BackTrack Five is significantly outdated and riddled with known security vulnerabilities. Running it in a production environment or using it for any unauthorized activities is highly discouraged and potentially dangerous. This article serves as a guide to installing BackTrack Five within a VMware virtual machine using an ISO image. This approach provides a safe, isolated environment to explore its capabilities, but should never be used for activities that might be construed as illegal or unethical.
Important Disclaimer: This guide is purely for educational and historical purposes. Installing BackTrack Five should only be done in a completely isolated environment, disconnected from any network containing sensitive data. BackTrack Five is outdated, contains numerous security vulnerabilities, and is no longer supported. Using it for any unauthorized activities is strictly prohibited and carries significant risks. We strongly recommend against using this operating system in any production environment.
The Path Before You Begin
Before embarking on this journey into the past, it’s essential to prepare the necessary tools and ensure your system meets the minimum requirements. We also want to take the time to underscore again the dangers and risk of using Backtrack 5 in today’s security landscape. Please carefully consider the risks before moving forward.
First, ensure your hardware has sufficient resources. A minimum of two gigabytes of RAM is recommended, although four gigabytes or more will provide a smoother experience. You’ll also need adequate hard drive space, at least twenty gigabytes, to accommodate the operating system and any tools you plan to install. Finally, your processor must support virtualization technology. This feature, often labeled as VT-x for Intel processors or AMD-V for AMD processors, must be enabled in your computer’s BIOS settings.
Second, gather the required software. You’ll need VMware Workstation Player, which is free for non-commercial use, or VMware Workstation Pro, a paid option offering advanced features. Most importantly, you’ll need the BackTrack Five ISO image, the installation file for the operating system. We will discuss downloading this image shortly.
Finally, a basic understanding of virtual machines will be beneficial. Familiarity with concepts like virtual hardware, networking modes, and snapshotting will make the installation process smoother and help you troubleshoot any issues that may arise.
Obtaining the BackTrack Five ISO Image
Downloading the BackTrack Five ISO image is perhaps the most critical step, fraught with potential security risks. Given that BackTrack Five is no longer actively maintained, many unofficial websites may offer the ISO image bundled with malware or other malicious software. Therefore, exercising extreme caution and verifying the integrity of the downloaded file is paramount.
We strongly recommend obtaining the ISO image from a reputable source, if possible, such as the Internet Archive. If downloading from another source, proceed with extreme caution.
Verifying the ISO Image’s Authenticity
After downloading the ISO image, before proceeding any further, it’s crucial to verify its authenticity. This is done using a cryptographic hash function, specifically SHAtwohundredfiftysix, which generates a unique “fingerprint” of the file. If the downloaded ISO image has been tampered with or corrupted, its SHAtwohundredfiftysix checksum will differ from the official value.
To calculate the SHAtwohundredfiftysix checksum, you can use built-in tools in your operating system. On Windows, you can use the certutil command in the Command Prompt:
certutil -hashfile path\to\your\iso\file.iso SHA256On Linux or macOS, you can use the sha256sum command in the terminal:
sha256sum path/to/your/iso/file.isoAfter running the command, compare the generated checksum with the official checksum provided by the source from which you downloaded the ISO image. If the checksums do not match, immediately delete the downloaded ISO image. It is likely to be corrupted or tampered with and could pose a security risk to your system. If you can’t find the correct SHA checksum, then we recommend not using the ISO and using a modern operating system instead.
Creating Your Virtual BackTrack Five Environment
With the verified ISO image in hand, you’re ready to create a new virtual machine within VMware. Open VMware Workstation Player or Pro and select “Create a New Virtual Machine.”
Choose the “Custom (Advanced)” installation option. This allows for more granular control over the virtual machine’s configuration.
On the “Choose Hardware Compatibility” screen, select VMware Workstation eight point x or later. This ensures compatibility with the older operating system.
Select “I will install the operating system later” and choose “Linux” as the Guest Operating System. For the version, select “Other Linux two point six point x Kernel sixtyfourbit (or thirtytwobit, depending on your ISO image).”
Give your virtual machine a descriptive name, such as “BackTrack Five Virtual Machine,” and choose a location to store its files.
Allocate processor cores to the virtual machine. Generally, one or two cores are sufficient.
Allocate memory. Two gigabytes is the minimum, but four gigabytes will provide better performance.
For the network type, choose “Use network address translation (NAT).” This allows the virtual machine to access the internet through your host computer’s connection. This is helpful, but again, we highly recommend to never connect this to a production or private network.
Select “LSI Logic” as the I/O controller type. This is generally the recommended option for compatibility.
For the disk type, select “IDE.” This is important for compatibility with BackTrack Five.
Choose “Create a new virtual disk.” Specify a disk size of at least twenty gigabytes and select “Store virtual disk as a single file.” This makes the virtual machine easier to manage.
Finally, choose a name for the virtual disk file and click “Finish” to create the virtual machine.
Installing BackTrack Five from the ISO Image
Now that you’ve created the virtual machine, it’s time to install BackTrack Five from the ISO image. Select the virtual machine in VMware and click “Edit virtual machine settings.”
Select “CD/DVD (IDE)” and choose “Use ISO image file.” Browse to the downloaded BackTrack Five ISO file and ensure “Connect at power on” is checked.
Power on the virtual machine. It should boot directly from the ISO image.
At the boot menu, select “BackTrack Text – Default Boot Text Mode.” While the graphical installer is available, the text mode is often more reliable for older systems.
After the system boots, log in with the default credentials: username root and password toor.
If you chose the textmode installation, start the graphical installer by typing startx and then running the installer icon on the desktop.
Follow the on-screen installation instructions. Select your language, keyboard layout, and hostname. When prompted for disk partitioning, choose “Guided – use entire disk.” Write the changes to disk.
When prompted to configure GRUB, select “Yes” to install the GRUB boot loader to the master boot record (MBR).
Once the installation is complete, reboot the virtual machine.
PostInstallation Configuration
After the reboot, log in as root with the password toor. The first step is usually to update the system, but this is where things get tricky. BackTrack Five is no longer supported, so the default repositories may be unavailable or broken. Proceed with caution if you choose to update the system.
To update the system, run the following commands:
aptget update
aptget upgradeBe prepared for errors if the repositories are no longer accessible.
If necessary, configure networking. You can usually accept the default settings.
If you wish, you can attempt to install VMware Tools. This may improve performance and integration with the host operating system, but compatibility is not guaranteed. To install VMware Tools, mount the VMware Tools CDROM image from within VMware, copy the installer to a temporary directory, extract the installer, and run the installation script.
Finally, it is strongly recommended to change the default password for the root user. To do this, type passwd and follow the prompts.
Important Considerations and Troubleshooting
Using BackTrack Five comes with significant security risks. The system is outdated and contains known vulnerabilities. Do not use it for any unauthorized activities or on any network containing sensitive data.
Be aware that the default repositories may no longer be working. This can make it difficult to install software or update the system.
VMware Tools compatibility is also a potential issue. The latest version of VMware Tools may not work correctly with BackTrack Five.
If you encounter boot problems, you may need to reconfigure GRUB. If you experience networking problems, check your network settings in VMware. If you have graphical interface issues, try reinstalling the graphics drivers.
Alternatives to BackTrack Five
Given the security risks and limitations of BackTrack Five, we strongly recommend using a modern penetration testing distribution like Kali Linux. Kali Linux is actively maintained, receives regular security updates, and includes a wide range of up-to-date penetration testing tools.
Kali Linux offers a much more secure and reliable platform for learning and practicing cybersecurity skills. It also has a large and active community, providing ample support and resources.
In Conclusion
Installing BackTrack Five in a VMware virtual machine can be a worthwhile exercise for educational and historical purposes. However, it’s crucial to understand the inherent security risks and limitations of using an outdated operating system. This article provided a stepbystep guide.
Remember to use BackTrack Five only in a safe, isolated environment and never for any unauthorized activities. Prioritize your security by using a modern, supported distribution like Kali Linux for your penetration testing endeavors. The digital landscape is always evolving, and you should equip yourself with the best and safest tools to explore it responsibly.
Further learning resources include the official Kali Linux documentation and various online penetration testing tutorials. Continue exploring, learning, and practicing your cybersecurity skills in a safe and ethical manner.
