In concert with oxygen, soil alkalinity strongly restricts the availability of iron, an essential nutrient with a multitude of functions in living organisms. In addition to its role in mitochondrial energy metabolism and as a cofactor for enzymes, in plants iron also plays key roles in photosynthesis and is required for chlorophyll biosynthesis. The ability to thrive in calcareous soils, referred to as calcicole behaviour, is the readout of an amalgam of traits of which efficient foraging of iron is a decisive factor. Recently, the well-established concept of two distinct iron uptake strategies, phylogenetically separating grasses from other land plants, was expanded by the discovery of auxiliary mechanisms that extend the range of edaphic conditions to which a species can adapt. Secretion of a tailor-made cocktail of iron-mobilising metabolites into the rhizosphere, the composition of which is responsive to a suite of edaphic and internal cues, allows survival in calcareous soils through a competitive iron acquisition strategy, which includes intricate interactions with the consortium of associated microorganisms in, on, and around the roots. This versatile, reciprocal plant-microbiome interplay affects iron mobilisation directly, but also collaterally by impacting growth, fitness, and health of the host. Here, we review the mechanisms and the multifaceted regulation of iron acquisition in plants, taking into consideration the specific constraints associated with the uptake of iron from alkaline soils. Knowledge on how plants extract iron from such soils sets the stage for a better understanding of essential ecological processes and for combatting iron malnutrition in humans.