Smart Cities have been around as a concept for quite some time. However, most examples of Smart Cities (SCs) originate from megacities (MCs), despite the fact that most people live in Small and Medium-sized Cities (SMCs). This paper addresses the contextual setting for smart cities from the perspective of such small and medium-sized cities. It starts with an overview of the current trends in the research and development of SCs, highlighting the current bias and the challenges it brings. We follow with a few concrete examples of projects which introduced some form of “smartness” in the small and medium cities context, explaining what influence said context had and what specific effects did it lead to. Building on those experiences, we summarise the current understanding of Smart Cities, with a focus on its multi-faceted (e.g., smart economy, smart people, smart governance, smart mobility, smart environment and smart living) nature; we describe mainstream publications and highlight the bias towards large and very large cities (sometimes even subconscious); give examples of (often implicit) assumptions deriving from this bias; finally, we define the need of contextualising SCs also for small and medium-sized cities. The aim of this paper is to establish and strengthen the discourse on the need for SMCs perspective in Smart Cities literature. We hope to provide an initial formulation of the problem, mainly focusing on the unique needs and the specific requirements. We expect that the three example cases describing the effects of applying new solutions and studying SC on small and medium-sized cities, together with the lessons learnt from these experiences, will encourage more research to consider SMCs perspective. To this end, the current paper aims to justify the need for this under-studied perspective, as well as to propose interesting challenges faced by SMCs that can serve as initial directions of such research.