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I’m having difficulties installing a Windows 8.1 trial on my late-2009 iMac. I had Vista installed a little while back, but think I installed this when my iMac was running Snow Leopard (it’s since been upgraded to Mavericks).

I’ve created two DVDs: one with the Windows trial ISO, and one with the ISO converted to a .crt file. Boot Camp complains that this Mac can only run Windows 7, and also recognises neither of these as installation disks; it just keeps telling me to insert the installation disk and wait a few moments.

So I’ve tried re-booting my iMac and holding down the Alt key, but it doesn’t pick up the optical drive; it just displays two hard drive partitions (Macintosh HD and Recovery). (It also doesn’t detect the partition I’ve set aside for Windows, but I guess that’s because it’s formatted as ExFAT).

I’m therefore out of ideas as to what to do, in that I’ve resorted to trying to install Windows in a VM. This isn’t ideal, as I wanted to be able to boot into Windows and use it just as I would OS X, not through virtualisation on an OS X desktop.

So…

  1. What am I doing wrong with Boot Camp, and why does it not recognise neither the burned ISO or .crt DVDs as installation disks?
  2. If there’s nothing I can do with Boot Camp, is there any way I can take the image of my Windows VM, and apply it to the partition set aside on my iMac’s hard drive so I can boot into it?
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If you don't want to have a separate OS, Parallels Desktop for Mac puts a virtual window on your Mac Desktop with Windows. A free alternative is VirtualBox although requires more computer knowledge.
To help your issue without using Parallels, try using a USB drive.

  • Good answer ! Keep it up and keep sharing your knowledge, our site grows from the contributions of those like you ! – 123456789123456789123456789 Dec 22 '17 at 12:23
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If you do NOT want a virtual instance of Windows and you want to boot into Windows 8, you will have to use bootcamp.

  1. This is version of Boot Camp you should be using for Windows 8 (64-bit): Boot Camp Support Software 5.0.5033
  2. Try creating a Bootable USB / Pen Drive of Windows 8 (64-bit) and try booting through the drive using Alt: Here is the Guide to creating a bootable Windows 8 (64-bit) drive.
  3. If all is well, this should work like a charm. I am currently using Windows 8 Pro (64-bit) on my Macbook Pro, and it works like a charm.
  4. If you are using Windows 8 (32-bit) you might run into issues with bootcamp. Try 64-bit!: Here is the documentation you might want to refer.
  • I don’t have a USB stick which is why I’ve tried creating a boot DVD, but neither of my DVDs with the ISO and CRT files are picked up by Boot Camp as installer CDs. – Martin Bean Jul 16 '14 at 12:50
  • Create a DVD using a Windows 8 (64-bit) iso, using disk utility; And it should work. – aliasgar Jul 17 '14 at 7:34
  • Tried that, as above. I wrote the ISO to the DVD, but it’s not bootable. – Martin Bean Jul 17 '14 at 9:11
  • Try booting a Live CD / DVD of Ubuntu or any other Linux. This should boot ur PC directly into Linux. If it boots, there is an issue with you iso image / cdr image. I am assuming you have the Genuine DVD of Windows 8 (64-bit). Please try with the Genuine DVD instead of making an iso / cdr file out of it, and re-writing it on another DVD. – aliasgar Jul 17 '14 at 9:16
  • I’ve lost the disc, hence trying to burn another. – Martin Bean Jul 17 '14 at 10:30
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The CD/DVD it prompts you to make contains the drivers for Windows 7/8. You do not boot from it. You boot from Windows installer disc instead.

Once installed, you load the disc you burned to install the drivers.

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If you did not create the disk with the ISO using a direct byte for byte copy, it won't work. I do not know how to do that on Windows, but I'm sure there's a way, but on Linux or Mac OS it is easy, run this in a shell:

sudo dd if=PATH_TO_ISO of=DISK_PATH

where PATH_TO_ISO is the path to the ISO file, and DISK_PATH is the path to the disk. Be sure to use the right disk path, or VERY bad things can happen, you can rewrite your hard drive. To find the disk path on Mac OS, take out all USBs and disks, then run

sudo diskutil list

and note all the disks that show up (ex: /dev/disk0; /dev/disk1). Now insert the USB or disk, and run

sudo diskutil list

again. A new disk should appear. Use its path (ex: /dev/disk2) as DISK_PATH in the dd command. Never use /dev/disk0 or /dev/disk1, that is your HDD or SSD. Try it again using the disk created by the dd command. The command takes a long time to run, but you can check its progress by pressing ctrl+t. If this does not work, you could try installing rEFInd boot manager, which may aid you in booting from the partition bootcamp creates, but will not allow you to boot windows without a hybrid MBR (bootcamps way of allowing windows, which only accepts MBR partitions, to boot on Mac disks, which are often GPT partition schemes). There is a possibility to format an external drive (USB or HDD) to MBR partition scheme (you can even use DiskUtility for this), and install windows on it using the previous dd command. I have no idea if this would work, so do more research on it, but dd is how you would install Linux from an ISO to an external drive, so it may be similar.

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Disc Utils should be enough to burn a functional DVD, you can use Toast Titanium. But in case you can use VM Windows, or an actual Windows machine use Rufus.

In the pass the only things that caused this behavior was:

  • Bad batch of DVD's
  • "Unattended" Windows Edition
  • Unproperly burned iso

Also i think the key you should press on boot, is "C" and not "Option". C is gonna give you a menu with everything bootable. I might be wrong, been a while since my macbook died on me.

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