The research is an attempt to find a deeper understanding of concepts that have emerged in our current time, forming a challenge to the existing legal rules. The use of digital systems by countries’ military forces and their employment in armed conflicts raised questions and challenges for the rules of international humanitarian law, especially regarding the extent to which these rules can respond to such challenges. The research addressed two main challenges: the legal classification of cyber operations in terms of whether they are considered attacks according to the general concept of an attack, and the issues faced in applying the principle of proportionality in cyber operations as outlined in Article 49 of Additional Protocol I. The arguments used to justify taking these operations out of the scope of international humanitarian law are not well-founded, as international legal rules can rely on the Martens Clause of humanity to address any gaps whenever they fail to apply to new variables. The research tries to find proper legal approaches to consider a cyber operation as an attack based on legal determinants presented by scholars. It also aimed to give the principle of proportionality a broader understanding in cyber operations, criticizing those who try to limit the principle to traditional military operations. All of this leads to conclusions and proposals to address these two challenges.