Mostly just writing this so I can keep notes.
Today I came up with the idea to forcibly put the WPAD entry into a Windows Domain’s DNS. For those who don’t know what this would do there is an entire Wikipedia article on the subject: https://en.wikipedia.org/wiki/Web_Proxy_Autodiscovery_Protocol
I did this via PowerShell pretty easily on one of the domain controllers like so:
PS C:\> Add-DnsServerResourceRecordA -Name wpad -ZoneName sittingduck.info -IPv4Address 107.
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