On 22 December 2017 Microsoft Corporation ("MS") filed a lawsuit (Microsoft Corporation v. John Does 1-10 using IP address 73.21.204.220, (United States District Court, Western District of Washington at Seattle. Decided 2 Jan 2018, Microsoft Corp. v. Doe, CASE NO. C17-1911RSM) (the "MS case"). The suit alleges large-scale copyright infringement through software piracy and trademark infringement relative to Microsoft registered trademarks. What was unusual about this filing is that MS, at the time of filing, had nothing more on which to base its lawsuit than an IP address that had communicated over 28,000 times with its registration servers in Seattle. I discuss this in the first section discussing the MS Case. In 2017, Kristanalea Dyroff sued Ultimate Software Group, Inc for the death of her son due to a drug overdose. She contended that her son – 29 years old at the time – was guided to a dealer of fentanyl-laced heroin based upon recommendation from Ultimate’s proprietary machine learning (ML)-based tool that guided users to things on its website that might interest them. Although it could have been a major effort at applying the law to ML-based software, it failed because the judge failed to address the ML aspect directly. Instead, the court analyzed the case based upon conventional law and precedent. Likewise, the issue of personal jurisdiction in cyberspace was not, but should have been, addressed. A discussion with one of the attorneys for the plaintiff conducted by the author the week of 19 April 2021 confirmed that, in the attorney's opinion, the court erred in finding for the defense. This paper analyzes the jurisdictional and technical issues raised by these two types of cyber event and postulates the jurisdictional and technical challenges raised by next generation cyber events that employ artificial intelligence ("AI"), particularly machine learning ("ML") through the lens of two cyber case analyses.

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Corresponding author. Peter Stephenson: pstephen@cdfs.us

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