We live in an era of an intrusive, comprehensive regulatory state. In this world, it is increasingly easy to break the letter of the law without the intention of wrongdoing, and a proliferation of government agencies has led to a proliferation of codified rules regulating not only our commerce, but large swaths of our civic life. We retain, theoretically, the option to remain outside the ambit of much federal and state regulation -- but this is a false hope.This Comment reacts to this proliferation of regulations by proposing a humane and rational attitude, to be consciously adopted by representatives of the regulatory state, both at headquarters and on the front lines. That attitude is one of guided discretion, that is to say, the conscious allocation aforehand of authority between an agency’s central office and its front-line employees, combined with principles and guidelines for line staff to use in making exceptions from their standard operating procedures in the course of enforcing their legal mandates.In particular, I show how administrative agents are similar to prosecutors in the criminal justice system, who already exercise effectively a healthy dose of the sorts of programs that I recommend. And I demonstrate the aptness of this comparison by showing how similar are prosecutorial activity and administrative enforcement and rulemaking activities.As a touchstone for my argument, I will juxtapose two agencies, one an example of the non-use and misuse of discretion, and the other an example of pragmatic and visionary government charting a better way. The former is the Transportation Security Administration (TSA). The latter is U.S. Immigration and Customs Enforcement (ICE), also part of the Department of Homeland Security, which guards our nation’s borders and enforces our immigration laws. While the TSA has adopted a take-no-prisoners attitude against snow globes, cupcakes, toothpaste, and bottled water, ICE has wisely recognized its limits, and decided to deploy limited resources in a more constructive manner, by focusing on dangerous aliens rather than illegal immigrants of a more benign kind.