Microsoft vs. MikeRoweSoft (2004)
en.wikipedia.org
en.wikipedia.org
AFAICT Microsoft simply had a relationship with a Canadian law firm who was effectively the IP equivalent of an ambulance chaser to pad their billable hours and they went after the kid.
I kinda doubt anyone important at Microsoft was even really aware of the situation until the easy-to-sell David v Goliath news story about it went viral.
https://www.huffpost.com/entry/michael-bloomberg-nyc-domain-...
> Nissan Motors v. Nissan Computer was a lengthy court case between the two parties over use of the name Nissan and the domain name nissan.com.[2] The case has received national attention in the U.S.
Edit: This is one-sided but provides some more detail: https://web.archive.org/web/20220306225900/https://www.diges...