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It was to my understanding that using Generalize will cause the system to ignore hardware changes and treat the hardware currently installed as the original hardware. However, I’m running in to an issue where these computers are no longer accepting the current hardware and I’m being forced to enter the key again.

I’ve been using this as a guide as I’ve never used Sysprep for a rollout like this one.

Could it be that the HDD’s are causing the hardware detection to trigger? I find it hard to believe since I’m pretty sure it only happens when the Mother Board changes. However I’m at my wits end and I can’t for the life of me figure out what I’m doing wrong.

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Reset to default
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Sysprep with the Generalize switch will reset the activation clock. You can only reset the activation clock 3 times (unless you are using a KMS key). Is it possible that you have sysprepped more than 3 times? If the activation grace period has expired, you will be prompted for a Product Key as soon as the computer boots. You can check the grace period by running slmgr /dlv from a command line. I have two articles to help you understand this better: Work with Product Keys and Activation and How Sysprep Works (scroll down to the ‘Resetting Windows Activation’ section).

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