Learn How To Install Windows Server 2008 R2 Standard Or Datacenter Edition On VirtualBox 6.1

Windows Server 2008 R2 is a widely used enhanced version of Windows Server 2008 and had  improvements on REMOTE DESKTOP SERVICES, an improved version of HYPER-V, ACTIVE DIRECTORY and more! It is server side operating system that can be used for many use cases such as a FILE STORAGE & FTP server, a web server for hosting web pages, a database server for hosting Microsoft SQL Server databases, a network operations server for handling network functions such as DNS and  DHCP,  a PRINT SERVER for sharing and managing printers on a network. If you would like to learn how to use and configure Windows Server for any use case, you may need to purchase a computer. However a much simpler solution would be to install Windows Server as a virtual machine on a computer that you already have. Read this tutorial to learn how to install Windows Server Standard or Enterprise edition on Oracle VM VirtualBox 6.1. We have also included links to where you can download everything that is needed to complete this tutorial successfully. You can also watch a free video tutorial hosted on youtube as many times as you like and at any point in time. Click on the button below to watch it now!


In order to complete this tutorial successfully the following is a list of items that may be needed. Please ensure to have these items available before taking implementation action on this tutorial:
1) A desktop or laptop with a dual core processor, 4GB of RAM and atleast 50GB of free disk space
2) Windows 7, Windows 8, Windows 10 , MacOS 10.13 High Sierra or newer, or any linux based distro with a graphic user interface
3) Oracle VM VirtualBox 6.1 or newer
4) VirtualBox Extension pack
5) The Windows Server 2008 R2 standard or enterprise edition disk image file (ISO file)


1) Download the Windows Server 2008 from the internet archive.
2) Download and install VirtualBox 6.1 on to your computer
3) Open VirtualBox and create a new Windows Server virtual machine
4) Power on the virtual machine and install Windows Server 2008 R2
5) Install virtual box guest additions for Windows Server 2008 R2 and configure a VirtualBox shared folder.

Step 1: Download The Windows Server 2008 R2 Disk Image File From The Internet Archive

1) Windows Server 2008 R2 is no longer officially supported by Microsoft and this means that end users will no longer get free security updates, non security updates and free support options. Microsoft also no longer offers most download options and you would have to obtain Windows Server from alternative sources.

The internet archive is a website that keeps an archive of the web and you can find out of date and out of support downloads there. Click HERE to go to the Windows Server 2008 R2 download page.

2) An alternative would be to purchase a Windows Server 2008 R2 dvd or USB drive from a local IT SOFTWARE reseller near you or on e-commerce stores such as the amazon online store and ebay

Step 2: Download And Install VirtualBox 6.1 On To Your Computer.

3) VirtualBox can be download for free from the official virtualbox website. Go to and click on the DOWNLOAD VIRTUALBOX button on the home page.

Your web browser will redirect to a download page and just below the VIRTUALBOX PLATFORM PACKAGES section, there are download links for all supported operating systems. Click on the link for your operating system to start downloading virtualbox.

4) The installation process of virtualbox is not the same for all operating systems however in this tutorial we shall demonstrate the installation of virtualbox on MacOS. 

Open FINDER and go to the downloads folder, or the folder were VIRTUALBOX was downloaded to. Double click on the virtualbox.dmg file and double click on the VIRTUALBOX.pkg file. 

5)  A popup message will be displayed notifying you that MACOS will run a check to determine if VIRTUALBOX can be installed. Click on CONTINUE to run the check.

If no error message is returned the popup message will close and you can click on the CONTINUE button to the VIRTUALBOX installer to proceed. 

6) Click on the INSTALL button and a system security popup message will be displayed requesting that you enter your password to authorize the virtualbox software installation. 

Enter your password on the PASSWORD field and click on the INSTALL SOFTWARE button. 

7) The virtualbox installer will display a message notifying that the software installation has been successful. Click on the CLOSE button, go to the applications folder and launch the VIRTUALBOX application. 

Step 3: Create A New Windows Server Virtual Machine.

8) On the VIRTUALBOX menu bar, click on MACHINE > NEW to open the virtual machine creation wizard.  The wizard can also be opened by clicking on the  NEW button on the VIRTUALBOX tool bar.

9) The virtual machine creation wizard supports two modes for virtual machine creation, GUIDED MODE and EXPERT MODE. The EXPERT MODE is a much faster way of creating a virtual machine and to use it, click on the EXPERT MODE button.

Enter a name for the virtual machine on the NAME text box, select a folder to save virtual machine files on the MACHINE FOLDER file selection box and set the TYPE to MICROSOFT WINDOWS.

Set VERSION to WINDOWS 2008 (64 BIT) and use the MEMORY SIZE slider to allocate 2048MB (2GB) of RAM to the virtual machine.

Click on the CREATE A VIRTUAL HARD DISK NOW radio button and click on CREATE.

10) A popup box will be displayed prompting you to set the size and file type of the virtual hard disk. Set the FILE SIZE to 30GB and the HARD DISK TYPE to VDI (VIRTUALBOX DISK IMAGE) and click on the CREATE button.

Step 4: Power On The Virtual Machine And Install Windows Server 2008 R2

10) Right click on the virtual machine and click on START > NORMAL START. When the virtual machine starts a popup message will be displayed prompting you to select a virtual optical disk or physical optical drive. 

Click on the yellow file selection button, browse to the folder where the Windows Server disk image file and click on OPEN

11) Select the disk image file for the NOT ATTACHED list and click on the CHOOSE button.

12) Click on the START button to allow the virtual machine to boot up using the Windows Server disk image file.

13) When the boot up process completes a INSTALL WINDOWS program will open, select ENGLISH on the LANGUAGE TO INSTALL drop down menu, set the TIME AND CURRENCY FORMAT to ENGLISH (UNITED STATES), set the KEYBOARD OR INPUT METHOD to US and click on NEXT

14) Next, you will see a list of Windows Server editions that you can choose, there should be Standard, Enterprise and Datacenter editions. Select  WINDOWS SERVER 2008 R2 STANDARD ( FULL INSTALLATION) or WINDOWS SERVER 2008 R2 ENTERPRISE (FULL INSTALLATION) and click on NEXT

15) Microsoft requires that you accept the SOFTWARE LICENSE TERMS for Windows Server 2008 before you start the installation process. Click on the I ACCEPT THE LICENSE TERMS check box and click on NEXT

16) Next, the INSTALL WINDOWS program will request that you select the type of installation that you would like to do. Since this is a new installation of Windows Server click on the CUSTOM (ADVANCED) option. 

17) Select the virtual hard drive labelled as DISK 0: UNALLOCATED SPACE and click on NEXT

18) The INSTALL WINDOWS program will display the installation progress. Wait for the installation process to complete. The virtual machine may restart several times during installation.

19) Next, set a password for the Windows Server Administrator account on the password fields provided and click on the blue arrow button.

Step 5: Install Virtual Box Guest Additions For Windows Server 2008 R2 And Configure A VirtualBox Shared Folder.

20) The next step is to install virtual box guest additions for Windows Server 2008 R2. This will add features such as FULL SCREEN mode and shared folders.

On the virtualbox menu bar, click on DEVICES > INSERT GUEST ADDITIONS CD IMAGE. 

Open the windows file explorer, click on COMPUTER and double click on CD DRIVE (D): VIRTUALBOX GUEST ADDITIONS.


22) Next, the setup program will ask that you choose a installation location. We recommend that you leave it to the default location and click on NEXT.

23) On the CHOOSE COMPONENTS step, you choose to install DIRECT3D SUPPORT and START MENU ENTRIES. We also recommend that you leave the default selections as they are and click on INSTALL.

24) During the installation progress a popup message will be displayed prompting you to confirm if you would like to install the device software. Click on the ALWAYS TRUST SOFTWARE FROM ORACLE CORPORATION checkbox and click on INSTALL.

25) Once the installation is complete, click on the REBOOT NOW radio button and click on FINISH.

26) Avirtualbox shared folder allows you can access files of your host system from within a vitual machine. The shared files physically reside on the host and are then shared with a VM, which uses a special file system driver in the VirtualBox Guest Additions Software to talk to the host.

Shutdown the virtual machine, right click on it and select SETTINGS. Click on the SHARED FOLDERS tab and click on the ADD FOLDER button.

27) Choose a folder on your computer that you would like to be able to access from with the Windows Server virtual machine on the FODLER PATH file selection box. Click on the AUTO MOUNT check box and click on OK. Click on OK on the SETTINGS window to apply changes.

28) Start the virtual machine and open the windows server file explorer, and click on NETWORK. You should see a network folder name VBOXSVR and if you double click on the folder you should see the files saved on your host computer.