Installation of Windows and Linux on a Virtual Machine Using VMware Player

What is a Virtual Machine

VMware Player is a program which emulates hardware with a system UEFI/BIOS that is suitable for the OS being installed in question. This allows one to install another Operating System, the guest Operating System which acts as an application window within the host PC. Because the hardware is virtualised to be suitable to the guest OS in question, it can also be used to install a legacy operating system which has no driver support for newer hardware.

This is incredibly powerful when one wants to run software that is only compatible with a Legacy Version of Windows or test another type of Operating System. For example a scanner with drivers and software for only Windows XP may be ran on a Windows XP Virtual Machine that runs on a Windows 10 Host.

Installing VMware Workstation Player

VMware Workstation Player 16 can be installed on Windows 10 (64 Bit only) or a Ubuntu 20.04 or other Linux Distribution host PC:

For VMware to run smoothly it is recommended to have a PC that has at least a 6th generation Intel i5 Processor, 8 GB of DDR4 RAM and a 250 GB SSD (with 120 GB of free space).

Windows 10

Microsoft Windows 10 Development Virtual Machines

The primary Windows 10 Activation Mechanism is Hardware Based. When a new Virtual Machine is created, the Windows 10 installer will see the Virtual Machine as New Hardware. This thus results in Microsoft Product Activation mechanism issues when using a Retail License. Windows 10 VMs are commonly used for software testing and development. After listening to developer feedback, Microsoft have made a number of "throwaway" Virtual Machines available to download essentially for software testing. These expire in 50 days at which point you can just download a more up to date Virtual machine to use instead:

For a VM that doesn't expire you'll instead need a Full Retail License. Linking the Retail License to a Microsoft Account will partially alleviate Microsoft Product Activation issues.


A Virtual Machine is a great way to try Linux without interrupting your Windows Install. The Linux Kernel 5.x has been updated to include out of the box support for VMware and there is no complication with VMware tools when using the latest version of VMware Workstation Player 16 like there used to be with Linux installs.

The most commonly used Linux Distribution is Ubuntu 20.04. Mint 20 uses the Cinnamon desktop user interface which many people prefer to the Ubuntu GNOME3 user interface when using only a mouse and keyboard. However it performs worse than Ubuntu when used with a touchscreen and 2 in 1 device due to a poorly implemented touchscreen keyboard. DeepIn 20 has the closest user interface to Windows but is a Chinese based Linux distribution. This gives it out of the box update issues and store issues due to the update servers being in China. It is also behind Ubuntu when it comes to Touchscreen Keyboard.

Fedora 32 is recognised by VMware and setup in a very similar manner to Ubuntu 20.04. Most other Linux distributions won't be recognised such and will require the user to configure a VM in a similar manner to that shown in the Mint 20 guide for example Manjaro 20.1.

Legacy End of Life Windows

The most common legacy Windows versions required for legacy software and legacy hardware are Windows 7 Pro and Windows XP Pro. The biggest difficulty for these OS is obtaining the installation media and activating. I describe the best ways using OEM Downgrade Rights from a Windows 10 Pro OEM License.

Windows 7 Pro

For Windows 7 Pro you can either perform a clean install and activate using OEM Downgrade rights from a Windows 10 Pro Host PC for product activation by porting the SLIC 2.1 across. Or alternatively use VMware vCenter Converter to create a Virtual Machine image of the physical machine and activate using OEM Downgrade rights from a Windows 10 Pro Host PC for product activation by porting the SLIC 2.1 across.

Windows XP Pro

Unfortunately the popular Operating System Windows XP is not yet abandonware and the website WinWorld cannot host the Windows XP Installation ISOs. I suspect it'll be at least another 10 years until Microsoft allow them to upload the ISO for this OS. However as a workaround we can download Windows XP Mode and convert it to a Virtual Machine for use in VMware Player.

There is an official activation mechanism for this but it will only work on a Windows 7 Pro, Windows 7 Ultimate or Windows 7 Enterprise Host and not of Windows 10 Pro (despite it being a free upgrade from Windows 7 Pro). On a Windows 10 Pro OEM PC we can install a Windows 7 Pro VM and then install the XP Mode VM within it as a Nested VM that will remain activated.

VMware Tools Error

Legacy Windows versions required Legacy Drivers provided in the form of VMTools. If you get the following error message when attempting to install VMware Tools you will need to download the VMTools ISO and mount it directly:

VMware: Could not find component on update server. Contact VMware Support or your system administrator.

Windows Abandonware

The website WinWorld hosts installation ISOs and Product Keys for Windows versions which are over 20 years old. These can be installed in VMware Workstation Player. I have wrote a guide for Windows 98SE and some additional notes as I needed Windows 98SE to revive an old scientific instrument when I worked at a University. There are no Product Activation issues on such Abandonware.

Windows 2000

Windows 98SE

Converting CD/DVDs into ISO Images and Floppy Disks into FLP Images

In many cases you may need to convert physical media to file that can be copied over to your Windows 10 Host PC and loaded as a Virtual CD/DVD or Virtual Floppy Drive. Use WinImage for CDs and Floppy Drives. I think the free version has an upper size limit so use ImgBurn for DVDs (note some Security Products such as Malwarebytes Antimalware dislike ImgBurn as its installer included an optional toolbar).

One thought on “Installation of Windows and Linux on a Virtual Machine Using VMware Player

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.