Chapter 1 examines street policing, particularly stop-and-frisk and its close twin, pretextual misdemeanor and traffic stops. The racial, individual, and collective costs of these policing practices have been well documented. Less widely noticed is the contrast between the Supreme Court’s consistently lax treatment of pedestrian and traffic stops and its more recent tendency to strictly regulate technologically enhanced searches that occur outside the street policing setting – searches that, coincidentally or not, are more likely to affect white people and the middle class. This chapter argues that if, as the Court has indicated, electronic tracking and searches of digital records require probable cause that evidence of crime will be found, stops and frisks should also be prohibited unless the police have probable cause to believe that a crime has been committed or attempted (in the case of street detentions) or that evidence of crime will be found (in the case of post-detention searches of people and cars). It also argues that this equalization of regulatory regimes not only fits general notions of fairness but is mandated by the Court’s cases construing the Fourth Amendment’s Reasonableness Clause, which endorse a “proportionality principle” that requires that the justification for a search or seizure be roughly proportionate to its intrusiveness.