The chapter examines the legal and extra-legal difficulties in eliminating military objectives. It also attempts to verify the claim,often made in literature on the subject, that civilians account for the majority of victims of armed conflict. The review of legal complexities begins with the examination of the principle of proportionality, the requirement to take appropriate cautionary measures, and the prohibition of reprisals. Extra-legal difficulties include the following issues: the shift in the nature of contemporary armed conflict; the tendency to protect one’s own troops at the expense of other goals; the trend to deliberately attack populations perceived as vulnerable; using gender as a potential cause for targeting; insufficient precision of weapons used in action; and difficulty in obtaining reliable information on the status of a person or object.