This article explores the problem of social integration from a positio
n of isolation. It uses the experiences of high school undercover offi
cers to consider the problem conceptually. Officers must move from new
student to peer to drug purchaser without any informant assistance an
d with severe time constraints. Three specific techniques are used to
trigger this process: class clowning, retreatism, and troublemaking. E
ach is a variation on the single theme of rebellion. I argue that thes
e techniques generate interpersonal familiarity a from a distance by c
reating reputations that drug dealers identify with and vest legitimac
y in. Reputation substitutes for introductions informants could otherw
ise give, establishes a pretransaction comfort zone, and lays the inte
rpersonal groundwork officers need before they can solicit drugs. Offi
cers' behavior is conceptualized through the notion of a cognitive bri
dge, a hybrid of interactionist and microstructural principles. Data a
re drawn from interviews with thirty undercover officers who operate f
rom a large western U.S. municipality.