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Coyotes (Canis latrans) are highly adaptable, medium-sized carnivores that now inhabit nearly every large city in the United States and Canada. To help understand how coyotes have adapted to living in urban environments, we compared two ecologically and evolutionarily important behavioral traits (i.e., bold-shy and exploration-avoidance behavior) in two contrasting environments (i.e., rural and urban). Boldness is an individual’s reaction to a risky situation and exploration is an individual’s willingness to explore novel situations. Our results from both tests indicate that urban coyotes are bolder and more exploratory than rural coyotes and that within both populations there are individuals that vary across both spectrums. Bolder behavior in urban coyotes emerged over several decades and we speculate on possible processes (e.g., learning and selection) and site differences that could be playing a role in this behavioral adaptation. We hypothesize that an important factor is how people treat coyotes; in the rural area coyotes were regularly persecuted whereas in the urban area coyotes were rarely persecuted and sometimes positively rewarded to be in close proximity of people. Negative consequences of this behavioral adaptation are coyotes that become bold enough to occasionally prey on pets or attack humans.