This chapter identifies and explores a central feature of automated legal guidance: “simplexity.” As this chapter introduces this term, simplexity occurs when the government presents clear and simple explanations of the law without highlighting its underlying complexity or reducing this complexity through formal legal changes. Automated legal guidance inherently relies on simplexity as a result of the tension between the complexity of the law and the need of agencies to explain the law in simple terms. In creating the law, the federal government must address complex problems, and it often does so by creating legislation that is replete with errors, ambiguities, and problems. This disconnect between complex federal law and agencies’ need to explain the law to the public in simple and understandable ways forces agencies to rely on simplexity. Automated legal guidance only exacerbates the need for simplexity, because when individuals use automated online tools offered by government agencies, they expect the explanations to be even simpler, more straightforward, and easier to apply than would be the case if they were relying upon written agency publications.