In the past two decades, a large amount of attention has been devoted to the introduction of smart manufacturing concepts and technologies into industrial practice. In Europe, these efforts have been supported by European research and innovation programs, bringing together research and application parties. In this paper, we provide an overview of a series of four content-wise connected projects on the European scale that are aimed at advancing smart manufacturing, with a focus on connecting processes on smart factory shop floors to manufacturing equipment on the one hand and enterprise-level business processes on the other hand. These projects cover several tens of application cases across Europe. We present our experiences in the form of a single, informal longitudinal case study, highlighting both the major advances and the current limitations of developments. To organize these experiences, we place them in the context of the well-known RAMI4.0 reference framework for Industry 4.0 (covering the ISA-95 standard). Then, we analyze the experiences, both the positive ones and those including problems, and draw our learnings from these. In doing so, we do not present novel technological developments in this paper—these are presented in the papers we refer to—but concentrate on the main issues we have observed to guide future developments in research efforts and industrial innovation in the smart industry domain.