1. I bought and installed Parallels Desktop on my Mac.
  2. I installed Parallels Transporter Agent on my Windows machine that runs Windows 7.
  3. I migrated my windows machine to my Mac, took about 36 hours. I can see on my mac desktop all of the files and folders that are on my windows desktop.
  4. After that was done, the virtual machine says "Upgrading Windows", and below that, per the title of this post, it says "Preparing to configure your virtual machine..."
  5. It chugs for about a minute, and the progress bar gets about 1/5 of the way.
  6. It stops and now the virtual machine screen is black, except for: "Windows. Click to Start." If I click on that, it goes back to step 4.

Alternative: On step 4 above, there is a little icon, and if I click on it, it asks me: "Are you sure you want to switch to the manual configuration mode for the "Windows" virtual machine? If I click "Yes" to that, something else happens each time! One of the following 3 things happens:

(a) I get a screen that says "Starting Windows". But after a few seconds, a get a blue screen, and it jumps back to step 4 above.

(b) I get a black screen that says at the bottom "Windows is loading files" that lasts a few seconds; then a progress bar at the bottom that also lasts a few seconds; then I get a blue screen (not the blue screen of death) with what looks like a little black dos popup which lasts just a second; then I get a little wizard popup entitled "Startup repair" which also lasts just a second; then another little popup that lasts less than a second, then back to step 6 above.

(c) I get a black screen entitled "Windows Error Recovery", which gives me two options:

(c.i) Launch Startup Repair (Recommended). Choosing this does the same as (b) above.

(c.ii) Start Windows Normally. Choosing this does the same as (a) above.

Mac OS X Yosemite Version 10.10 iMac 27-inch


  • Same problem in 10.11 and Parallels 11, except on #4 it goes to a help page on the Parallels site and I can't really do anything else. VMware seems to start up, but has a horrible problem where it can't seem to shrink volumes properly now and was hoping to move over to Parallels for this customer. C'est la vie. – ylluminate Sep 5 '15 at 18:34
  • Well, finally I was able to bounce around a couple of times and I found that I was able to reclaim space with Parallels (even though it would not start the OS) and then import to VMware and now I have this client using VMware instead of Parallels with a savings of about 60GB to boot. – ylluminate Sep 5 '15 at 19:09

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