Apparently the VMware tools installed on Ubuntu 11.10 and some other versions of Linux are not able to shrink an ext4 disk partition. http://www.insomnihack.com/?p=387 To do it another way, first fill up the empty parts of the virtual disk with zeros: # This step is optional, but can eliminate some apt package files and # save some disk space. % sudo apt-get clean # This step is also optional, but can help identify apt packages # taking up the most disk space. Source: # http://www.commandlinefu.com/commands/view/3842/list-your-largest-installed-packages-on-debianubuntu % sed -ne '/^Package: \(.*\)/{s//\1/;h;};/^Installed-Size: \(.*\)/{s//\1/;G;s/\n/ /;p;}' /var/lib/dpkg/status | sort -n # bs=20megabytes is simply the block size that will be written at a # time. The command below will copy 2 megabytes of 0 bytes from # /dev/zero at a time to the file /0bits, until the virtual disk is # full. sudo dd if=/dev/zero of=/0bits bs=20971520 # Now remove that file. sudo rm /0bits After you've executed these commands, shutdown your VM and use vmware-vdiskmanager to shrink the virtual drive file. Windows instructions: cd "C:\Program Files\VMware\VMware Workstation" vmware-vdiskmanager -k path\to\your\VirtualDisk.vmdk On my Mac: cd ~/Virtual Machines.localized/Ubuntu 11.04 32bit.vmwarevm # With VMware Fusion 4 # also works with VMware Fusion 6, although file name may be something like Virtual\ Disk.vmdk /Applications/VMware\ Fusion.app/Contents/Library/vmware-vdiskmanager -k Ubuntu\ 11.04\ 32bit.vmdk # Older cmd line with VMware Fusion 3 /Library/Application\ Support/VMware\ Fusion/vmware-vdiskmanager -k Ubuntu\ 11.04\ 32bit.vmdk