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How to reinstall Windows 8.1 on Bootcamp?

I am trying to reinstall Window 8.1 on Bootcamp after Disk Utility reported that the hard drive it was originally located on was failing and needed to be replaced. I did so. Now when Windows 8.1 installer launches, it thinks I'm doing an upgrade and insists that I "reboot Windows Normally" and then launch the Installer, which is impossible because it's freshly formatted, NEW hard drive.


Here are the steps that I followed:

1) Disk Utility reports that Boot Camp drive is failing and replace it.

2) Remove failing hard disk, replace with new one.

3) Launch Bootcamp Assistant.

4) Download support drives to USB stick.

5) Begin install process using same Windows disk (64-bit FULL VERSION) used previously.

6) Windows Installer asks for Product Key.

7) I enter product key.

8) WIndows asks to agree to license terms.

9) Setup presents ONLY two choices:

Upgrade Installation

Custom Installation

10) I choose Upgrade.

11) Windows Setup reports that Upgrade can only take place from Windows environment, to eject Windows Install disk, and to reboot into Windows "normally." Cannot eject Windows install disk. Click Close box.

12) Windows Installer relaunches.

13) Install process starts over again.


Please note:

1) This is a fully licensed copy of Windows 8.1

2) I am using it on the same Mac as the original installation. Only change is the hard drive.

3) This is not an authentication issue. Windows accepts the Product Key.

4) Parallels is not involved in any way.


I have talked to several Windows support teams. None were helpful and ultimately said this was a Bootcamp/Apple problem


Apple Support was much more helpful but said they'd never encountered this problem before and were flummoxed.


I have reformatted the Bootcamp hard disk several times. At one point I thought the issue might be that the Mac still thinks the original Windows installation exists because I kept the same name for the new hard disk. Renaming and reformatting did not change the behavior.


Does anyone have any suggestions?

Mac Pro (Mid 2012), OS X Mavericks (10.9.1), 3.2 Ghz Quad Core Intel, 6GB RAM

Posted on Jan 7, 2014 12:32 PM

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Posted on Jan 9, 2014 3:23 PM

I wound up solving, or at least working around my problem. Selecting "Custom Install", instead of Upgrade, took me to a dialog box where Installer could format the Bootcamp drive from scratch. Installation then proceeded as expected. Unfortunately this cost me my partition, but that was better than being stuck in this Upgrade Catch-22. Note that formatting and partitioning this drive within the Boot Camp assistant did not solve my problem.

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Question marked as Best reply

Jan 9, 2014 3:23 PM in response to Walter Kilbourne

I wound up solving, or at least working around my problem. Selecting "Custom Install", instead of Upgrade, took me to a dialog box where Installer could format the Bootcamp drive from scratch. Installation then proceeded as expected. Unfortunately this cost me my partition, but that was better than being stuck in this Upgrade Catch-22. Note that formatting and partitioning this drive within the Boot Camp assistant did not solve my problem.

How to reinstall Windows 8.1 on Bootcamp?

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