With the increasing presence and importance of machine learning, artificial intelligence, and big data in our daily lives, there comes the necessity to re-evaluate how magical, enchanted lines of thinking may or may not survive alongside the turn of the century. There exists a set of connections between magic and the aforementioned field of technology, in that this specific field has the potential to become sufficiently advanced and complex as to cause unpredictable problems down the line. This discussion will explore several different topics ranging from the comparisons between magic and technology to the dangers of these systems being “black box” and rather ambiguous in how they turn data input into prediction output, all central to the idea that this increasingly tech-focused world should be thought about in a magical and re-enchanted way, especially as legislation is drafted up and decided upon that can determine how these impressive new technologies will be regulated going forward.