From hardening of marshmallow to graining of hard candies, moisture plays a critical role in determining the quality and shelf life of sugar-based confections. Water is important during the manufacturing of confections, is an important factor in governing texture, and is often the limiting parameter during storage that controls shelf life. Thus, an understanding of water relations in confections is critical to controlling quality. Water content, which is controlled during candy manufacturing through an understanding of boiling point elevation, is one of the most important parameters that governs the texture of candies. For example, the texture of caramel progresses from soft and runny to hard and brittle as the moisture content decreases. However, knowledge of water content by itself is insufficient to controlling stability and shelf life. Understanding water activity, or the ratio of vapor pressures, is necessary to control shelf life. A difference in water activity, either between candy and air or between two domains within the candy, is the driving force for moisture migration in confections. When the difference in water activity is large, moisture migration is rapid, although the rate of moisture migration depends on the nature of resistances to water diffusion. Barrier packaging films protect the candy from air whereas edible films inhibit moisture migration between different moisture domains within a confection. More recently, the concept of glass transition, or the polymer science approach, has supplemented water activity as a critical parameter related to candy stability. Confections with low moisture content, such as hard candy, cotton candy, and some caramels and toffees, may contain sugars in the amorphous or glassy state. As long as these products remain below their glass transition temperature, they remain stable for very long times. However, certain glassy sugars tend to be hygroscopic, rapidly picking up moisture from the air, which causes significant changes that lead to the end of shelf life. These products need to be protected from moisture uptake during storage. This review summarizes the concepts of water content, water activity, and glass transition and documents their importance to quality and shelf life of confections.