The synthesis of a supramolecular double hydrophilic glucose responsive block copolymer (DHBC) held together by cucurbit[8]uril (CB[8]) ternary complexation and its subsequent self-assembly into micelles is described. The supramolecular block copolymer assembly consists of poly(N-isopropylacrylamide) (PNIPAAm) and poly(acrylamidophenyl boronic acid) (PAAPBA) as temperature and glucose responsive blocks, respectively, and poly(dimethylacrylamide) (PDMAAm) as a hydrophilic block. Drug release studies of insulin-loaded micelles using three external triggers were studied with release of insulin achieved by changing temperature, glucose concentration or by adding a competitive guest for CB[8]. This system offers good control over the release of insulin under physiological conditions (pH 7.4, 37 °C). These exciting results suggest that this system could be a model for a clinically relevant drug delivery vehicle for diabetic treatment.