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Despite having over 3GB of available space, I am unable to install the DHCP server role.

This originally was a 10gb virtual box drive image, but when I ran into space issues extended the drive to 12gb. I've subsequently run chkdsk and defrag, to see if I could get Windows to recognize the available space.

Is there some way I can convince Windows Server 2012 I have enough disk space?

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    I'm not sure how applicable this is, but did you expand the NTFS partition to fill the rest of the disk? The disk may have been expanded, but you need to expand the partition to fill it.
    – Naftuli Kay
    Jul 23, 2014 at 17:08

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From TechNet on the absolute minimum requirements to run Server 2012 R2:

Be aware that 32 GB should be considered an absolute minimum value for successful installation. This minimum should allow you to install Windows Server 2012 R2 in Server Core mode, with the Web Services (IIS) server role. A server in Server Core mode is about 4 GB smaller than the same server in Server with a GUI mode. For the smallest possible installation footprint, start with a Server Core installation and then completely remove any server roles or features you do not need by using Features on Demand. For more information about Server Core and Minimal Server Interface modes, see Windows Server Installation Options.

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    Yeah, you're starving the VM for disk space. This is the correct answer.
    – jski
    Jul 23, 2014 at 15:01
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    I understand the sentiment of "there's no way the DHCP service can take up 3GB!," and it doesn't really, but please understand that this is not Unix or DOS. A lot of tangential things happen in the background any time something is installed or removed from a Windows system. Hundreds of Side-by-Side entries have to be updated, Windows Updates needs scratch space to update the role, etc.
    – Ryan Ries
    Jul 23, 2014 at 15:28
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    I also just want to add that even if you're able to squeeze out just enough free bytes by removing the GUI, compressing WinSxS, or whatever other off-route things you have to do, that might get it to technically work, but you'll always be putting yourself at risk of being out of support by going against published Microsoft minimum requirements for installing their OS. And IMO, that's what this site is about - professional, enterprise-grade systems administration, so vendor support is important.
    – Ryan Ries
    Jul 23, 2014 at 17:26

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