Smallholder farmers play an important part in the dairy value chain in Sub-Saharan Africa. Three technological approaches have been used to improve productivity. These are through, applying agricultural ecological processes (ecological intensification), utilising modern livestock breeding (genetic intensification), and socio-economic intensification. Ecological intensification includes continuous housing of cows applying a cut-and-carry feeding system, introduction of purpose-bred forages and pastures, and the introduction of agro-forestry within the dairy systems. Genetic intensification strategies include: importation of dairy breeds such as Holstein–Friesian (HF) and cross-breeding of the indigenous breeds with HF. Training and capacity-building activities to create sustainable livelihoods have been initiated for farming and technological practices of animal husbandry, but also to enhance appropriate leadership and corporative-building skills that would create and support an enabling environment for sustainability. These improvements and initiatives in the service delivery have been championed by national governments, development partner institutions, or non-governmental organisations through different programmes. Challenges of intensification include matching management to genetic potential of imported and cross-bred improved dairy breeds, ensuring low post-harvest losses, proper utilisation, and reducing environmental impact. Using examples from Kenya, Malawi, Mozambique, Tanzania, and Zambia, this paper reviews the management and assessment approaches used in fostering smallholder dairy development strategies and dairy’s contribution to sustainable livelihoods in the face of intensification.