This Dagstuhl Seminar Task and Situation-Aware Evaluation of Speech and Speech Synthesis is an opportunity to help redefine the metrics and methods traditionally used to evaluate speech synthesis and human speech as they are used across disciplines, tasks, and applications. The seminar is designed as a collaborative platform where experts from engineering, the humanities, social sciences, and more come together to challenge the status quo and drive innovation. Through the combination of perspectives and the bridging of gaps between scientific disciplines we hope to uncover and develop evaluation techniques that are not only scientifically rigorous but also contextually relevant to the diverse uses of speech technology today. We seek the collective expertise of participants from diverse areas of science and technology – ranging from phonetics to machine learning, from rhetorical analysis to practical applications in assistive technologies. This interdisciplinary approach is essential for crafting evaluation standards that are as dynamic and nuanced as the technologies and applications they aim to assess. To this end, we encourage you to share, debate, and refine ideas, methods, and tools that can contribute to a transformative discussion on the evaluation of speech synthesis.