The analysis of targeting in this article is divided into three parts. First, the nature of warfare as a State based activity and with it the impact the levels of war (e.g. strategic, operational and tactical) have on the application of air warfare is explored. Particular attention is paid to the development of airpower theory and challenges that arise in the use of airpower as a strategic “weapon”. As demonstrated, it is the application of airpower to meet strategic goals that has impacted on the legal definition of “military objectives” and with it the effort to limit collateral civilian casualties and damage. Secondly, the military doctrine governing the application of airpower is reviewed. The framework developed by State military forces to conduct air warfare not only demonstrates how airpower theory is put into practice it highlights a number of the challenges facing military forces seeking to apply targeting 'principles'. This part discusses the operational planning process; and highlights targeting doctrine such as effects based targeting, the phases of the targeting cycle, and time sensitive targeting. Thirdly, building on the preceding contextual development, the late 20th Century attempt to regulate targeting is discussed. Particular attention is paid to the two main trends applied in interpreting the legal definition of military objectives. One approach seeks to restrictively apply the wording of Additional Protocol I with a bias towards narrowly viewing lawful targets as being more directly associated with the tactical level of war fighting. The second broader method applies a more traditional strategic approach seeing warfare as a State based activity resulting in a broader set to targets that may be attacked. Ultimately, it is suggested the second method of interpreting the law governing what objects may be attacked more accurately reflects how air warfare is conducted and wars are fought. The analysis then turns to the requirements of the principle of distinction; the identification of people and objects as targets; the resolution of doubt; and application of targeting precautions, both in the offence and defence. The goal of this assessment is to outline the challenges associated with applying international humanitarian law provisions to the targeting decision-making process.