Figured out the problem. When building the WIE I had put the Universal Imagining Token. I remade the WIE and left the Universal Token blank and now it prompts for a users username and password.

@matiit
https://docs.theopenem.com/imaging/toec-image-prep.html
Example Sysprep Answerfile: https://docs.theopenem.com/imaging/toec-image-prep.html#sysprep-tab

I recently took over managing the imaging server at work and there isn't a ton of documentation from before my time that can help out with this. I was deploying images for about 2 months with no issues. One day I was uploading a new image and for some reason it no longer asks for login credentials when entering the imaging environment anymore. The only settings I had changed were the provision requirements. I have since gone back and tried every single combination and still hasn't worked. I have also tried rebuilding the WIE multiple times. Have not been able to get it back into a state where it prompts for a login. As a last resort I updated the server to 1.5.5.0 in hopes that there would be a fix for it but the issue still persist.

Thank you for taking the time out of your day to read this!
Kind regards
-Jarod K