This chapter describes the results of the authors' research of automated legal guidance tools across the federal government, conducted over a five-year period from 2019 through 2023. The authors first began this study in preparation for a conference on tax law and artificial intelligence in 2019, and were able to expand it significantly, under the auspices of the Administrative Conference of the United States (ACUS), in 2021. ACUS is an independent US government agency charged with recommending improvements to administrative process and procedure. The goals of this study were to understand how federal agencies use automated legal guidance and to offer recommendations based on these findings. During their research, the authors examined the automated legal guidance activities of every US federal agency. This research found that agencies used automation extensively to offer guidance to the public, albeit with varying levels of sophistication and legal content. This chapter focuses on two well-developed forms of automated legal guidance currently employed by federal agencies: the US Citizenship Immigration Services’ “Emma” and the Internal Revenue Service’s “Interactive Tax Assistant.”