The role of the lipophilic surfactant, polyglycerol polyricinoleate (PGPR) in water transfer in food-grade double emulsions was investigated, and related to physical emulsion stability. Double (W/O/W) emulsions were prepared with various PGPR concentrations (0.5–5.0 wt%) in the oil phase, at initial osmotic pressure differences of up to 1.1 MPa between the water phases. At high PGPR concentrations (>2 wt%), emulsions showed good physical stability, with encapsulation efficiency close to 100%. It was found that PGPR is involved in water transfer between the water phases through reverse micelle formation by PGPR molecules or hydrated monomers of PGPR, and this allows for controlled swelling. Emulsions that are initially of low viscosity (milk-like emulsions), obtain an apparent viscosity of up to 3 Pa·s, and this effect can be used to tune the emulsion properties to the targeted application, whithout the need to gel either the internal or external phase.