Classic theories of counterinsurgency claim rebel forces execute attacks in an unpredictable manner to limit the government’s ability to anticipate and defend against them. We study a model of combat and information-gathering during an irregular insurgency. We test empirical implications of the model using newly declassiﬁed military records from Afghanistan that include highly detailed information about rebel attacks and counterinsurgent operations, including close air support missions, bomb neutralizations, and covert government-led surveillance activity. Our conﬂict micro-data also include previously unreleased information about insurgent-led spy networks, where rebels monitor troop movement and military base activity, as well as military base inﬁltration and insider attacks. We couple these data with granular information on opium production and farmgate prices. Consistent with our simple theoretical model, we ﬁnd that the capacity (wealth) of local rebel units inﬂuences the timing of their at-tacks. As rebels gather more resources, their attacks become temporally concentrated in a manner that is distinguishable from randomized combat. This main eﬀect is signiﬁcantly enhanced in areas where rebels have the capacity to spy on and inﬁltrate military installations. Taken together, these ﬁndings suggest economic shocks that increase the capacity of insurgents may inﬂuence the timing of rebel attacks through the acquisition of precise information about military weaknesses.