Digital content management systems have enabled cultural heritage institutions and humanities researchers to create interactive, public‐facing, and open‐access scholarly work, including digital libraries, databases, archives, manuscripts, and collections. Exploratory tools have become a widely deployed feature of such digital projects that support in‐depth, creative interaction with digital materials. However, producing and managing a digital project with such tools can be complex, time‐consuming, and expensive, requiring significant financial investment, institutional support, and human capital. This has led to a critical need to evaluate the effectiveness of such embedded exploratory infrastructures across different stages of digital projects. This 90‐minute panel discussion aims to explore the questions of how to evaluate the use and effect of such exploratory infrastructures, from diverse perspectives of researchers, developers, and downstream users. The panelists will draw from case studies to address questions such as: (1) the perceived value and impact of embedded exploratory tools, (2) the involvement of communities and stakeholders in the evaluation process, and when to conduct such evaluations, (3) the methods and approaches to evaluation, and (4) the interpretation of evaluation outcomes. The discussion will also delve into the challenges and opportunities associated with evaluating embedded exploratory tools in digital projects and scholarship.