Both VMware Fusion and Workstation can give you the error “There is not enough space on the file system for the selected operation” if you expand the virtual disk of a virtual machine.
It occurs when there is less free disk space available on the host disk containing the virtual disk than the newly requested space of the virtual disk. In short: you must have enough room to store the original virtual disk plus the expanded virtual disk. This holds for VMware Player too.
This is a real problem if your main system has SSD only (like a Retina MacBook Pro) where there is an even bigger fight for disk space than HDD based hosts.
It is one of the reasons not only my main system has an SSD drive, but also an external USB3 SSD drive to temporarily make more room available.
–jeroen
The Wiert Corner - irregular stream of stuff 