Windows Server 101


  • Install VirtualBox on your computer.
  • Download the Windows Server 2019 Evaluation ISO file.
  • Create a new virtual machine (2 CPU, 4GB RAM, 50GB HDD/SSD).
  • Mount the ISO into the new virtual machine.
  • Boot the virtual machine and run through the initial setup.
  • The server will reboot.
  • You have a server to play with.

System Setup:

Host OS:
Windows 10 (1909)

VirtualBox 6.1

Virtual OS:
Windows Server 2019


Windows Server is an industry standard server operating system. If you are considering any carear path in IT its worth having a basic working knoledge of it.

In this guide I will talk you through how to setup a Windows Server within a virtual machine. You can then use this to play around with safe in the knoledge that you can not break anything important! If you do completely break it you can just delete it and build it again!

Where to run my virtual machine?

There is a lots of different options for running virtual machines (known as hypervisors). I am not going to cover these today as it could be a blog series in its own right! Today I am going to show you how to Install Windows Server 2019, using VirtualBox running on Windows 10. However, some really common options for people getting started are:

  • VirtualBox –
    • Pro: Free!
    • Pro: Simple to use.
    • Pro: Can be installed directly on your computer.
    • Con: Needs a medium or high end computer.
  • VMWare Workstation Pro –
    • Pro: Simple to use.
    • Pro: Can be installed directly on your computer.
    • Con: Expensive
    • Con: Needs a medium or high end computer.
  • ESXi Server –
    • Pro: Free!
    • Pro: Is the basic version of one of the most common hypervisors used in the industry.
    • Pro: Does not use any of the power from your computer.
    • Con: Requires its own computer to run on (if you have an old computer kicking around this is probably the perfect candidate!)
    • Con: Harder to setup but simple to use.

But Windows Server is REALLY expensive!

You are right, Windows server is really expensive. However you can download an evaluation version from the Microsoft website that you can run for 180 days. After this the server will start rebooting hourly. At this point you have a couple of options, you can either reinstall the OS and get another 180 days. Alternatively you can “rearm” the evaluation, you can do this up to 3 times.

Disclaimer: You should ensure that you have read the terms and conditions for Windows Server Evaliation. They are all important but you specificially need to ensure your justification you are running the software for is inline with the terms and conditions.

You can download the evaluation from This link is designed to be used in the UK. If you are based outside the UK you may just need to put “Windows Server 2019 Evaluation” into your search engine of preference.

Building the server.

Start by opening VirtualBox…

Click on the new button that will then open this screen where we can give some basic infomation about the name of the VM, where it will be saved and the OS type & version.

We then specify how much RAM we want to give the server. I normally aim for 4GB for lab servers with a GUI. A GUI is the “point and click” interfaces that your computer probably has. Instead of the CLI thats the “lines of green text” like in the matrix!

We now need to say that yes, we need a hard drive and we want to create it now.

We then specify if we want it to be dynamically allocated or fixed size. The wording provided is already solid so I am not going to try and re-explain it! In labs I tend to go for “Dynamically allocated”.

We then specifiy how big we want the hard drive to be. This is how much space you have to store the operating system, programs and files etc. The default of 50GB for most lab setups is fine.

Once we hit create the wizard will close and our new virtual machine will be visable. Now we need to take the Server 2019 ISO (think of this like a virtual DVD) file we downloaded earlier and “mount” it into the virtual machines drive. Start by selecting the virtual machine on the left (mine is blue so its already selected). Then click the orange settings “gear” icon.

This will open the settings page where we can then navigate to the “Storage” settings on the left hand side. We then click on the “Empty” option with the blue disk next to it. We now get an “Attributes” section on the right hand side with another blue disk.

We need to now click this blue disk. Then select the “Choose/Create a Virtual Optical Disk…”. We can also just select “Choose a disk file…”, to be honnest I’m not sure why I didnt do this!

Having clicked “Choose a disk fileā€¦” we then need to click the “Create Option”. This will open a file explorer and you need to select the ISO file thats probably in your downloads folder.

After this we will see the file in the list. We can now select this and click choose.

We will now see the virtual disk file has been mounted into the drive as it is no longer “empty”. We have now finished with the settings and can click “Ok” at the bottom.

This will now bring us back to the VirtualBox software where we can click the “Start” button.

This will open a new Window that essentially shows you a virtual screen for your virtual machine. Note: If you click into this window your keyboard and mouse will be “captured” by this screen. To release them you need to press the Right Ctrl button. This is what the warning bar at the top is telling us.

The virtual machine will then go through a few different screens as it boots up. It will eventually bring us to this screen where we can select our language / formats etc.

On the next page we want to click the install button.

We then want to select the Standard Evaluation (Desktop Experience). Remember what I was saying earlier about the CLI and GUI. The first option is for a CLI install, the “Desktop Expereince” option is for a GUI install. As this is your first dive into the world of Windows Servers I strongly recomend using a GUI. Note: In the real world you want to be using CLI severs. Therefore when trying things out try and use the GUI initially and then when you have it masted challagne yourself to do it in the CLI. You can access the CLI from the GUI, its called “PowerShell”.

You then need to read and, if you agree, accept the terms and conditions.

We then need to select the custom install option.

On this next page we can just click “Next”.

Then with no warning at all it will just start installing!

Once its rebooted we will be ask to set a password for the administrator account. You can then click finish.

You will then get the windows login page.

You will then want to press “Ctrl + Alt + Delete”. However you will find both your computer thats running virtual box and the virtual machine will respond. To get around this either press “Right Ctrl + Del” (this will send “Ctrl + Alt + Delete) to the VM for you. Alternatively you could open the input menu at the bottom (I am running full screen here).

Then Navigate to keyboard -> “Insert Ctrl-Alt-Del”.

We can now log into our new virtual machine.

Once we are in we should get something that looks like this.

Welcome to your first Windows Server experience. Have a look around, try every option you can find. Most importantly break every option you can find and workout how to fix it; this is when you will learn the most!


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