Tooth preparation is a common operation in dental clinical practice. This procedure is irreversible and invasive from the point of view of tooth preservation. Conditions of the abutment tooth, treatment methods, and restoration materials for target restoration affect tooth preparation. To achieve the goals of tooth tissue preservation, dental pulp protection, and periodontal health, dentistry professionals agreed on the importance of minimizing the amount of tooth reduction. The foundations for realizing this consensus are as follows. First, the available restoration materials with improved comprehensive performance need less target restoration space. Next, teeth can be prepared under a digital guide, and the real-time measurement of restoration space can be verified due to the invention of digital technologies for the analysis of the quantity and shape of the prepared tooth and tooth measurement. Moreover, guiding methods for preparation have been developed from freehand operation under the naked eye based on accumulated personal experience to digital-guidance jointing microscope. These innovations indicate the creation of a prototype of guided prosthodontics that is precise and applies real-time measurement throughout the process of tooth preparation. From the perspective of the evolution of digital, guided, and micro prosthodontics, this article raised seven questions about the numerical value and quantitative data transfer of tooth preparation and evaluated the authenticity of existing numerical requirements from the perspective of the four elements of measurement. Identifying unified measuring methods and developing measuring tools with a precision of hundred or ten microns will be the key to solving the problem about the authenticity of numerical measurement. Furthermore, this paper summarizes the methods of how to control tooth reduction and explains in depth why the currently dominant tooth preparation technology, which is based on empiricism, cannot effectively achieve the goals in digital prosthodontics. Therefore, we strongly call for rebuilding the digital foundation of prosthodontic treatment immediately.