Steps to Install Windows Server 2008 R2 on VirtualBox

This article shows how to install Windows Server 2008 R2 on VirtualBox. Windows 2008 R2 server is available in 64-bit version only, so your computer processor and motherboard should support 64-Bit architecture and VT (Virtualization Technology) to carry out this installation.

Even if you are using the 32-bit version of Operating Systems such as Windows 7, Vista and XP on the host computer, still it’s possible to use 64 Bit operating systems as a guest on VirtualBox. To make sure your computer processor and motherboard support this feature read this post where you will find relevant tools for AMD and Intel processors. Once the result confirms that your PC is 64-bit ready then you can proceed with the installation of Windows Server 2008 R2 on VirtualBox.

Follow the steps to Install Windows Server 2008 R2 on VirtualBox.

1) Create New Machine.

2) Select Windows 2008 R2 as the guest OS version.

Select Windows Server 2008 R2 on VirtualBox

3) Set memory size to 1024MB, and create a new hard disk with 20GB space. You can increase the RAM and hard disk size if your physical computer has enough resources.

Create new disk

Select the Dynamically Expanding storage option. Set the disk size and location of the disk file on the next screen.

Hard disk size

4) Press Finish to complete disk and virtual machine creation.

5) Click on the storage option in virtual machine configuration settings.

Storage controller option - Windows 2008 R2 on VirtualBox

6) Press ‘Empty’ IDE controller as mentioned below to insert the installation DVD or ISO image. If you have an installation DVD, then insert it into the host DVD drive and select the ‘Host Drive- Drive letter’ mentioned below. So when you boot the Windows 2008 R2 virtual machine, it will read your host physical DVD drive. Since I have an ISO file, I’m mounting it by clicking on the Folder arrow button.

Mount the CD

7) Make sure the following options are correct under system setting of the virtual machine. You can click on System to view the settings.

The System settings

Processor – 1 and Enable PAE/NX enabled.

PAE option for Windows Server

Hardware Virtualization Enable VT-x/AMD-V should be enabled.

Enable VT-X

8) Now start the Windows 2008 R2 virtual machine in VirtualBox.

The installation will go smoothly if all settings are correct. No need to explain every installation step.

Starting the installation

9) Here is the working Windows server 2008 R2 on VirtualBox below.

Install Windows 2008 R2 on VirtualBox

10) It is essential to install VirtualBox guest additions to get better mouse integration, display settings, folder share and improved network performance.  You can mount the built-in guest additions ISO file inside the guest VM from the menu bar.

Restart the virtual machine after the installation to see the changes & improvements.

virtualbox additions

There you go, you have the working Windows 2008 R2 64-bit Server OS on your X86 host OS and VirtualBox. You can enable the seamless mode of the virtual machine to work on Windows 2008 R2 VM  from the host OS desktop.

NOTE: Since Windows 2008 R2 is a pretty outdated server operating system currently, it is not recommended to use in the production environment. In case, you need to do some testing and development on this older server OS, you can use this guide to install it on a dedicated VirtualBox environment.

We highly recommend using the latest Windows Server Operating Systems, such as Windows 2022 or Windows 2019 servers. 

If any of the above solutions did not fix the Windows PC issues, we recommend downloading the below PC repair tool to identify and solve any PC Issues.

Dinesh is the founder of Sysprobs and written more than 400 articles. Enthusiast in Microsoft and cloud technologies with more than 15 years of IT experience.

28 thoughts on “Steps to Install Windows Server 2008 R2 on VirtualBox”

  1. I already installed a Linux server on Virtual box… but never thought of a windows server! 😀 This might be the perfect time for it! Thanks for the great post bro 😀

  2. I have VirtualBox 3.1.6 and in first drop-down list I have no option Windows 2008 (64 bit), only “windows 2008”. I guess it’s 32 bit OS. If yes, how do I install 64bit?

  3. I downloaded Intel Processor ID utility – it says my proc does support 64bit architecture. the problem is, it doesn’t support intel virtualization technology(VT). May be that’s the case?

  4. Glad to find this post it helped me a bit – proved I wasn’t crazy

    I was trying to install Windows 2008 R2 on X86 Sun VirtualBox on a fully patched new install of Solaris. I could load it and restart the VM a few times but once I powered it off and powered it on it failed. Loaded the OS about ten time (only takes a few minutes) but it always started ending up in a permanent “black screen” when powering up the VM.

    So I rolled back form VirtualBox 3.2.0 to VirtualBox 3.1.8 and it all worked fine. Obviously there is a bug in the latest release with respect to my OS and HW (stock sun). I used the exact same configuration (in this post) for both 3.1.8 and 3.2.0 – only 3.2.0 doesn’t work.

    #[3]: cat /etc/release
    Solaris 10 5/09 s10x_u7wos_08 X86
    Copyright 2009 Sun Microsystems, Inc. All Rights Reserved.
    Use is subject to license terms.
    Assembled 30 March 2009

    #[4]: uname -a
    SunOS mocrome 5.10 Generic_142901-02 i86pc i386 i86pc

    #[5]: prtdiag | head -2
    System Configuration: SUN MICROSYSTEMS SUN FIRE X4275 SERVER
    BIOS Configuration: American Megatrends Inc. 07060215 06/19/2009

  5. As you say at the begining:
    Even though you are running 32 Bit Operating Systems, such as 32 Bit Windows 7 ,Vista and XP as host, still it’s possible to run 64 Bit operating systems as guest on X86 VirtualBox.

    How???? Please ¡¡¡ Google doesn´t help :-((

    I have the same scenario as Gleb:

    Gleb says:
    April 26, 2010 at 3:04 am

    I have VirtualBox 3.1.6 and in first drop-down list I have no option Windows 2008 (64 bit), only “windows 2008″. I guess it’s 32 bit OS. If yes, how do I install 64bit?”

    Thanks in advance

  6. I was initially getting blue screen when trying to install Windows Server 2008 R2 64bit on VirtualBox. I ran across your article, followed the step-by-step guide, & the installation went smoothly. Thanks for taking the time to publish and share you knowledge!

  7. followed the instructions and by the step 5 I got an ide controller with cd/dvd empty and an sata controller with the hard disk of 20GB attached to it (server08r2b64.vdi), then on the empty cd at ide controller I chose the /home/lee/IT/MCSE/MS Tools/7600.16385.090713-1255_x64fre_server_eval_en-us-GRMSXEVAL_EN_DVD.iso and started the vm. it shows the initial screens of process installation to setup up language, time and keyboard and after hit “install now” right after pops up a screen saying that : “the cd/dvd drive device driver is missing. If you have a floppy disc,cd, dvd or usb flash drive please insert it now. It tells also that I can safely remove the windows cd of the cd/dvd drive”. under the message it presents three buttons: browse, ok and cancel.
    ????? host ubuntu 1004 kernel gpae, amd 9650, 4gram,

    • I have the same problem with missing drive device driver. Do you have found a solution?

      VirtualBox 4.0.8 r71778
      Host: Windows 7 (x64)

        • I have solved the problem by now. I have downloaded the ISO again. But now with Internet Explorer 9 (before with Chrome). ISO size is different. The new one is bigger. Now it works fine with VirtualBox. No more drive device driver problems during the installation.

  8. i am getting below error when trying the above steps

    VT-Xx/AMD-V hardware acceleration has been enabled, but is not operational. Your 64-bit guest will fail t detect a 64-bit CPU and will not be able to boot
    Please ensure that you have enabled VT-x/AMD-V properly in the BIOS of your host computer

  9. i m using windows 7 with 64 bit, i try to install windows 2008 64bit using virtual box, when i check in version column there is no windows 2008 64 bit, instead i am seeing only windows 2008

  10. we have installed windows 2008 64 bit on intel processor base system and created a virtual machine, it is good when we run intel processor base system the problem occur when we try to run the same virtual machine on AMD processor quad core system blue screen occur and virtual machine restart , is their any way to fix the problem.

  11. Hi

    at first thanks for this great article, it really help me, now I’m having an issue with windows installation, it seems that the installer is not recognizing the virtual disk for installation, I don’t know if someone has had the same issue as me, any help will be really appreciated.


  12. hi
    i install windows server 2008 (32bit) on my virtualbox 4.1.6 but the problem is that it couldn’t detect the network adapter . host os windows 7 on hp pavilion dm4.
    anyone can help plz

    • You should select the Intel PRO/1000 T Server adapter in the VBox GUI Windows Server 2008 should have a driver for that one.

  13. Hi

    i have recently installed Virtualbox on my Mac OS X (Lion) and also downloaded Windows Server 2008 R2, i have tried to install it into the Virtualbox, however after having followed all the instructions and ensuring all the settings are correct, it won’t install Server …a black box comes up with the following message: FATAL: No bootable medium found! System halted

    What does this mean? And what can I do to successfully install Server 2008 onto my Virtualbox please.
    Your help is most appreciated , many thanks

  14. Hi,

    Need some help. I installed virtualbox on windows xp Host OS. Installed windows 2008 server successfully on virtual machine with the above steps. Now i want to install Redhat linux also on the same virtual box. Can someone point me how to do that.


  15. You do all this great work and do not say anything about the most vexing thing of all – how the heck do you log into 2008 once it is installed. What is the osx key combo for ctrl + alt + del?

  16. In VirtualBox (Windows) CTRL+ALT+DEL is HOTKEY+DEL. The default hot key is RIGHT-CTRL. You can see the hot key down right in the status bar of your virutal machine.

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