I am currently trying to install a game that requires 46GB of space but parallels says I only have 26GB of space available. I have auto reallocation turned on, plus have 1.75GB of free space. Outside of this I tried manually switching it, resize file system is greyed out and in Disk Management when I right click on C Extend Volume is greyed out as well because the recovery partition is in-between drive C and the unallocated space so I cannot follow http://kb.parallels.com/en/113972 Any ideas? Never mind, I deleted the Recovery Partition using Diskpart which allowed me to extend the volume. I would still like to know why it isn't happening automatically like it has in the past.