We conducted a systematic review and inventory of recent research achievements related to spaceborne and aerial Earth Observation (EO) data-driven monitoring in support of soil-related strategic goals for a three-year period (2019–2021). Scaling, resolution, data characteristics, and modelling approaches were summarized, after reviewing 46 peer-reviewed articles in international journals. Inherent limitations associated with an EO-based soil mapping approach that hinder its wider adoption were recognized and divided into four categories: (i) area covered and data to be shared; (ii) thresholds for bare soil detection; (iii) soil surface conditions; and (iv) infrastructure capabilities. Accordingly, we tried to redefine the meaning of what is expected in the next years for EO data-driven topsoil monitoring by performing a thorough analysis driven by the upcoming technological waves. The review concludes that the best practices for the advancement of an EO data-driven soil mapping include: (i) a further leverage of recent artificial intelligence techniques to achieve the desired representativeness and reliability; (ii) a continued effort to share harmonized labelled datasets; (iii) data fusion with in situ sensing systems; (iv) a continued effort to overcome the current limitations in terms of sensor resolution and processing limitations of this wealth of EO data; and (v) political and administrative issues (e.g., funding, sustainability). This paper may help to pave the way for further interdisciplinary research and multi-actor coordination activities and to generate EO-based benefits for policy and economy.