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El Capitan and Windows 7 Legacy Dual Boot Broke

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.........

Hitting exit in Clover boots Windows...

72 hours later.

And I just figured out your problem: You had a OS X GUID/Windows GUID/MBR hybrid installation booting from Chimera/Chameleon.
You upgraded to El Capitan and installed Clover UEFI. Clover UEFI will not boot Windows on a hybrid GUID/MBR partition. Your best bet to prevent this kind of problem in the future is to go ahead and clone the Windows to the new SSD and reformat the old one for El Capitan. (or vice versa, which requires reformatting the old drive and re-installation of Windows)

Have you flashed your BIOS to latest version that allows booting UEFI? This may also be a contributing factor on a Z68 series board.
 
I was going to try cloning OS X to the new drive (my primary OS so I'd like more space) and migrating a copy of my Win partition, reinstalling Clover on the new drive, then once that is running wipe the old drive and clone Win 7 back to it.

Should I consider upgrading my MoBo to UEFI at this point or will it only cause trouble for my legacy installs at this point?
 
I was going to try cloning OS X to the new drive (my primary OS so I'd like more space) and migrating a copy of my Win partition, reinstalling Clover on the new drive, then once that is running wipe the old drive and clone Win 7 back to it.

Should I consider upgrading my MoBo to UEFI at this point or will it only cause trouble for my legacy installs at this point?

If you plan to continue with legacy installs there is no point to upgrading the BIOS to UEFI capable.
Just remember to install Clover in Legacy mode.
 
Thanks for all the help!

This machine is almost 4 years old and will probably be replaced in a year or two. I'll just wait to go UEFI on my next rig.

CCC is telling me it can't backup a bootable Windows. If I clone that Win volume with CCC to a formatted drive, and then run the Win startup repair, shouldn't that get it working?
 
Welp. FYI, migrating a Win 7 multi-boot install to a single boot drive is a pain-in-the-ass but I did it.

I had to manually create the system partition and then use a third-party application to write the boot files to it and configure its boot settings. It was compounded by having to juggle it around since I wanted to reuse the original drive. Having a spare drive for testing and installing is VERY useful for any install testing.

Clover won't let me get to the Win bootloader, even if I hit Exit now but it's fine because I can just use the BIOS to select the Win drive and it boots fine.

All worth not losing my set up. I primarily use my Win install for gaming so I didn't see much the benefit of doing a clean install. It was much more important for me to retain my setup. I'll fresh install next rig with a newer version of Win.

I wonder how I can fix Clover though. The issue must be related to UEFI. I must have installed the UEFI version like a dummy and my motherboard has reacted to it because all traces of my original bootloader were wiped in the drive moving process. I guess even though I don't have the latest UEFI firmware for my motherboard it was still able to react to UEFI software. *shrug* I'm tempted to try and upgrade the BIOS but I feel like I should just leave it since everything works fine now.
 
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