Sketching is an important activity for understanding, designing, and communicating different aspects of software systems such as their requirements or architecture. Often, sketches start on paper or whiteboards, are revised, and may evolve into a digital version. Users may then print a revised sketch, change it on paper, and digitize it again. Existing tools focus on a paperless workflow, i.e., archiving analog documents, or rely on special hardware—they do not focus on integrating digital versions into the analog-focused workflow that many users follow. We present the conceptual design and a prototype of LivelySketches, a tool that supports the "round- trip" lifecycle of sketches from analog to digital and back. The proposed workflow includes capturing both analog and digital sketches as well as relevant context information. In addition, users can link sketches to other related sketches or documents. They may access the linked artifacts and captured information using digital as well as augmented analog versions of the sketches. This data set contains supplementary material from a formative user study with four students (screencast and sketches created during the study).