Have you considered...

renaming "Reclaim hard drive space" "Completely Skrag Your Virtual Disk"? Because that's what it did to me twice tonight. Also the link to the forum page off the main support page is dead. http://forum.parallels.com/forumdisplay.php?58-Parallels-Desktop-for-Mac

My third windows install of the night is going into VMWare.

 

Hi,
Could you please elaborate what exactly has happened? Your virtual hard drive went down?
I doubt VMware does not have issues with reclaiming. VirtualBOX or any other soft can do the same.
If there is a mistake in the code, let us investigate it please.

 

1) I went to File: Free Up Disk Space
2) I chose "Reclaim disk space"
Both times, it panicked, tried to fix the disk, tried to diagnose and ultimately failed. I only pieced it together the second time that it's reclaiming disk space that's doing it.

 

Hm, ok.
Could you please run "Verify Disk" on your Mac system in Disk Utility?

/Applications/Utilities/Disk Utility.app -> choose Mac HD and click Verify Disk -> what will be the output?
And please create a problem report Help -> Submit a problem, please post its ID here if it is not much trouble for you.

 

A verify in Disk Utility is all OK/Green. Wow, so I did the report a problem thing and good thing I clicked to see the details. It just about sent a screen shot of all my work email to you*.

You guys can get to the bottom of this without me...

*You guys should be way more up front about what you're sending as part of bug reports. What you're doing is a giant F-up waiting to happen.