Nowadays, videos are the most prominent form of media. YouTube’s Chapters transformed the way videos are viewed online: from scrubbing the seeker-bar for thumbnails into a structured access to content. This paper suggests a semantic extension to this feature by requiring few additional annotations to be provided by content creators who are willing to increase their monetization potential. In turn, the added value of these annotations, called “Hidden Descriptors”, is phenomenal in terms of Semantic Browsing and Advertising. The Extended Chapters enable viewers to locate and browse specific segments of interest. Additionally, we suggest an advertisement positioning strategy that is both context-aware and adaptive to the Ads’ skippability. The conducted experiments highlight the efficiency and intuitiveness of the suggested semantic extension.