This chapter demonstrates the use of the proposed framework for digital work design and the embedded methods. It shows the mutual interplay of its components for articulating work knowledge, organizational learning, knowledge processing, and preserving design-relevant knowledge. The case studies describe the impact that could be generated through digital design support. The healthcare case demonstrates how meaningful work-model entities evolve in the course of articulation and guide aligned re-structuring of work. It stems from a complex planning process in clinical health treatment requiring the structured elicitation of contextual knowledge from all stakeholders involved to develop working procedures in time-critical situations. The CoMPArE/WP (Collaborative Model Articulation and Elicitation of Work Processes)-case has its focus on alignment when bridging from intuitive or semi-structured models to techno-centric (formal) models that can be executable for some workflow engine. The education case targets educator knowledge involving domain knowledge, didactic competence, and social skills. Finally, the Me2Me2You-case addresses mental model alignment of interaction behavior for executable workflow support from a cascaded interaction perspective.