If terrorist organizations wish to thrive, they often must adapt to lethal targeting. Over time, terrorist leaders can identify countermeasures that evade or erode state surveillance capabilities. Lower-level operatives will resist implementing these adaptations, however, so leaders must enforce their implementation. Leaders of groups with decentralized command relationships will struggle to directly monitor and enforce compliance. Leaders with limited resources at their disposal will also be unable to invest in the bureaucratic capacity to discipline operatives’ behavior. These organizational deficiencies become increasingly costly when state surveillance capabilities increase. I find support for this thesis by examining Arabic language correspondence from Usama bin Ladin’s compound related to the drone campaign in Pakistan. My argument contributes to theories of adaptation and the coercive power of warfighting technologies. It also suggests that advanced surveillance and strike capabilities may be insufficient for future counterterrorism success.