Interactions between salivary proteins and tannins are at the basis of one of the main mechanisms involved in the perception of astringency. Astringency is a tactile sensation evoked in the mouth by plant polyphenol-derived products, such as red wine. It is generally recognised that tannins can provoke negative sensations such as shrinking, drawing, or puckering of the epithelium. On the other hand, the astringency of some red wines can be felt as pleasant mouth feelings of richness, fullness, mouth-coating, and velvet in the mouth. In this chapter, an overview of the research concerned with molecular and sensory mechanisms of astringency was updated. Because of many variables influence the perception of astringency, several methods have been developed to measure the intensity of the sensation. In this context, different indirect assessments were critically evaluated considering the pros and contras and correlated with sensory analysis. We focused the attention on the saliva precipitation index (SPI), based on the binding and precipitation of human saliva with grape and wine tannins, because it has been widely used for many applications in winemaking. A current great challenge is to have an in vitro measurement of astringency able to provide information on the fate of wine, from grape to bottle.