This article evaluates the application of probation orders in Nigeria. It offers a detailed discussion of international legal frameworks for probation and in particular discusses penal provisions that provide for probation, while noting innovations provided by the Administration of Criminal Justice Act 2015, the Administration of Criminal Justice Laws of States and the Nigerian Correctional Services Act 2019. The article highlights the benefits, terms and conditions and duties of a probation officer and the application of probation in Nigeria. Complementarily, it discusses Kenya as a jurisdiction, where judicial activism and other underpinning factors have occasioned a robust application of probation. The article also identifies noticeable gaps which hinder the robust application of probation in Nigeria and proffers solutions by way of recommendations.