Oligomeric fatty acid esters, known as estolides, have been studied for close to a century. It has only been in the last few years, however, that efficient methods for preparing estolides have been developed that also allow some control over their molecular structures. By varying the bio-based feedstocks and reaction conditions, the functional properties, particularly those geared toward lubrication, can be modified. More recently, synthetic advances have permitted stepwise construction of estolides with functional groups (hydrophilic or reactive) positioned at specific sites within the chain.