As Boko Haram continues to evolve, especially in ideology, tactics, and objectives, such change has called into question how and why this has accrued. Through a qualitative analysis, this study examines key transformations in Boko Haram’s evolution with a view of identifying catalysts driving this change. Findings indicate that Boko Haram has undergone four phases of evolution and are linked to Nigeria’s security intelligence agencies’ counterstrategy and operational countermeasures, concluding this to have resulted from a failure of military and civilian expertise within Nigeria’s security intelligence agencies as well as interagency rivalry and a lack of cooperation, cohesion, and oversight.