This chapter roots the authors' insights about automated legal guidance in a broader examination of why and how to address the democracy deficit in administrative law. As this chapter contemplates the future of agency communications, it also explores in greater detail the possibility that technological developments may allow government agencies not only to explain the law to the public using automated tools but also to automate the legal compliance obligations of individuals. While automated legal compliance raises serious concerns, recent examples reveal that it may soon become a powerful tool that agencies can apply broadly under the justifications of administrative efficiency. As this chapter argues, the lessons learned from our study of automated legal guidance are critical to maintaining values like transparency and legitimacy, as automated compliance expands as a result of perceived benefits like efficiency.