Global rapid transformations require continuous and systematic adaptations of organizations. To this end, intangible assets play a central role in organizational sustainability and competitiveness. Considering the intrinsic elements of the company’s structure, corporate relationships, and professionals, knowledge is considered a critical success factor. Due to various reasons, this knowledge can be lost over time, posing an organizational risk. To mitigate the impact, it is relevant to create reactive and preventive actions. The risk of knowledge loss is constant and, therefore, needs to be assessed more dynamically. It is important to consider some seemingly contradictory but complementary aspects, such as knowledge gains. Analyzing the relationship between knowledge losses and gains from the perspective of intellectual capital enables the management of intellectual capital to create strategies for maximizing knowledge gains in the face of the risk of loss. Leveraging gains can provide conditions for organizations to remain enduring and adaptive. Therefore, the central objective of this chapter is to analyze how scientific studies relate to knowledge losses and gains and how they are interrelated with the intellectual capital of organizations. It aims to classify knowledge losses and gains within the structures of intellectual capital to identify new approaches to intellectual capital management, considering the analysis of knowledge assets in an expanded manner. Intellectual capital management practices are presented as a way to actively address these contradictions.