The benefits of teacher-facing dashboards are incontestable, yet their evidence is finite in terms of long-term use, meaningful usability, and maturity level. Thus, this paper uses design science research and critical theory to design and develop TEADASH to support teachers in making decisions on teaching and learning. Three cycles of design science research and multiple small loops were implemented to develop the dashboard. The tool was then deployed and evaluated in real time with the authentic courses. Five courses from two Swedish universities were included in this study. The co-design with teachers is crucial to the applicability of this dashboard, while letting teachers use the tool during their courses is more important to help them to recognize the features they actually use and the tool’s usefulness for their teaching practices. TEADASH can address the prior matters, align with the learning design, and meet teachers’ needs. The technical and co-design aspects, as well as the advantages and challenges of applying TEADASH in practice, are also discussed here.