Volume to Volume fails to boot

I’m using Winclone 8.0.1 to clone a Windows 7 environment to a new iMac (2019) running 10.14.6 as primary OS. The clone initially failed, but after looking at the logs I determined that the target volume size was too small (even though it was already larger than the old volume). I repartitioned into a larger volume and the clone proceeded and completed.

Now however, while the Windows volume shows up in the Startup Disk pref and while option booting, it does not boot into Windows. After choosing it while option booting, it reverts back to the Mac volume and boots to the Mac desktop; choosing the Win volume in Startup Disk progresses to a black screen that goes nowhere (after waiting at least 15 minutes) necessitating a power cycle.

Any suggestions would be appreciated.


I don’t think the iMacs 2019 support Windows 7.