Spider silk is a protein material that exhibits extraordinary and nontrivial properties such as the ability to soften, decrease in length (i.e., supercontract), and twist upon exposure to high humidity. These behaviors stem from a unique microstructure in combination with a transition from glassy to rubbery as a result of humidity-driven diffusion of water. In this Letter we propose four length scales that govern the mechanical response of the silk during this transition. In addition, we develop a model that describes the microstructural evolution of the spider silk thread and explains the response due to the diffusion of water molecules. The merit of the model is demonstrated through an excellent agreement to experimental findings. The insights from this Letter can be used as a microstructural design guide to enable the development of new materials with unique spiderlike properties.