This review examines the prospect of improving perennial legume adaptation to grazed mixed pasture swards across the higher-altitude regions of south-eastern Australia through improved management, particularly as it relates to soil fertility. The range of adapted perennial species available to farmers often remains limited to only one perennial forage legume species, white clover (Trifolium repens L.). Despite recent advances in cultivars for increased persistence in dryland environments, white clover remains sensitive to drought with its inherently shallow root system and limited capacity to restrict water loss from herbage. With few alternative species likely to become widely available in the foreseeable future, prospects for extending the boundaries of perennial legume adaptation likely rely on a dual approach of improving soil fertility and further genetic improvement in white clover. Improved soil fertility would focus on overcoming soil acidity and addressing nutrient deficiencies, particularly of phosphorus, potassium, boron and molybdenum, which tend to be more widespread in the target region. Addressing these soil constraints would alleviate periodic moisture stress by: (1) increased water availability through improved infiltration and soil hydraulic properties; (2) increased root growth to maximise exploration of the soil volume; and (3) better maintenance of plant cell structures to foster improved osmotic regulation. However, the extent to which white clover adaption may be extended remains an issue of further research. This review highlights an opportunity for further genetic improvement of white clover by focusing on improving the capacity to recover from periodic droughts through seedling regeneration. Further breeding efforts in white clover should examine the feasibility of selecting for hard seed characteristics more similar to the best-adapted subterranean clover (Trifolium subterraneum L.) cultivars across this region to promote ongoing seedling regeneration.