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Hi jacobtvpuckett! I think this could be a few things.
- Do you have any firewall rules on your system that would prevent WinRM traffic? Packer would need to be allowed to send WinRM to the network interface that is being used by the VM. I believe it should be HTTPS traffic over port 5986 based on this line: https://github.com/cisagov/prescup-challenges/blob/main/pc4/vm/win10/scripts/bios/autounattend.xml#L153
- There could be a certificate trust issue. If you are using a company machine that has certificate policies in place, then your machine may not trust the self-signed certificate that the VM uses for WinRM. That certificate is generated here: https://github.com/cisagov/prescup-challenges/blob/main/pc4/vm/win10/scripts/bios/autounattend.xml#L136
Hope that helps a bit! If not, and you're willing/able to paste the logs or packer output, I might be able to better see what could be going on.
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