The present chapter, after providing an excursus of the milestones that led to the adoption of Article 52(2) of API, aims to address some crucial issues concerning the definition of military objectives, focusing in particular on the assessment of the “military advantage” and the controversial notion of “attack as a whole”, which appear to be of particular relevance when dealing with dual-use objects. To this end, the chapter will discuss the difficulties of making clear determinations on how to plan and carry out military operations within the bounds of the law as enshrined in Article 52(2) of API and customary IHL. In this regard and to offer practical examples to rely on, the analysis will consider the controversial findings on the qualification of military objectives presented in the award on the aerial bombardment of the Hirgigo Power Station, issued by the Eritrea-Ethiopia Claims Commission (the Commission, or EECC), and in the so-called “Goldstone Report” released by the UN Fact Finding Mission on the Gaza Conflict. Furthermore, a working definition of “dual-use objects”, which takes into consideration all the pressing issues discussed thus far, will be presented to lay the foundations for the paradigm shift discussed in the next chapters.