When confronted with mass uprisings, governments deploy their security forces for crowd control or repression. However, sometimes security agencies choose to side with the opposition movement. Recent work shows that “fragmentation” contributes to defection: fragmenting the security forces into parallel units leads to oversight problems and grievances among soldiers, which raises the risk of members of the security forces defecting to the opposition movement. However, I argue that the effect on defection is strongly moderated by the circumstances under which states choose to fragment their military: fragmentation for the purpose of security specialization, called “differentiation,” even decreases its risk. Employing Bayesian multilevel modeling, the findings corroborate this distinction. The study contributes to the fundamental discussion on civil–military relations, shedding light on why some conflict situations see security defections while others do not. Understanding this phenomenon is a pivotal element to explaining how conflicts develop, escalate, and end.