I use VM Ware on my Macbook Pro / Air and have had issues with some BB's and not others, but it was definitely due to the VM Ware /Windows setup. Same happened on another one of my MacBook's that night - and when I went to a Windows 7 PC, it worked flawlessly. It would never reconnect on JVM. This was on OS6 on a 9700. OS7 on the 9900 worked on the same Macbook/ VM Ware machine the same day. I'm guessing that's where you're getting stuck. You could probably tweak the USB settings in the Parallels installation and perhaps get it going...but I'm not really sure. These Windows emulator software's are not perfect. When they work, they blow away a Windows PC, but when they don't...
I use VMware fusion and occasionally it will fail after the reboot if the phone doesn't reconnect. If I am paying attention when it doesn't reconnect, I can just click the usb icon for the virtual machine then select connect BlackBerry device and the install will continue. If I am doing something else and miss it not reconnecting, the upgrade will fail.
the best solution I have had is to use the Windows 8 consumer preview on my early 2009 macbook using boot camp. I have loaded 4 different os versions and it works great.
The download is completely free, you get to play around with the preview version of windows 8, and you get the full functionality of desktop manager.
I didn't want to keep having to use someone else's pc, nor did I want to shell out money for parallels and a version of windows just to be able to update my blackberry.
Thanks for the great suggestion on Win8 consumer preview, just curious how does one download and have it installed on bootcamp? I recall bootcamp required me to insert a disk with Windows to complete the installation, no?
