The glucose-sensitive delivery system holds great promise as a therapeutic approach for high-incidence diabetes due to its ability to release insulin whenever elevated glycemia. However, it still faces the instability problem under hyperglycemic environment, which leads to the short time of sustained insulin release. Herein, we designed dually-crosslinked insulin polyionic micelles (DCM@insulin) based on triblock polymers of o-glycol and phenylboronic acid-functionalized poly(ethylene glycol)-poly(dimethylamino carbonate)-poly (dimethylamino-trimethylene carbonate) (mPEG-P(AC-co-MPD)-PDMAC and mPEG-P(AC-co-MAPBA)-PDMATC, respectively) for sustained glucose-responsive insulin release. DCM@insulin with phenylboronic acid ester structure (first crosslinking structure) enhanced glycemic responsiveness by regulating insulin release under hyperglycemic environment. Additionally, the UV-crosslinking structure (second crosslinking structure) by the residual double bonds in AC units endowed DCM@insulin with the ability to effectively protect the loaded insulin against protease degradation and avoid burst release under multiple insulin release. The in vivo findings demonstrated that DCM@insulin effectively maintained glycemic levels (BGLs) within the normal range for 6 h in comparison to single-crosslinked micelles (SCM@insulin). Therefore, the glucose-responsive and dually-crosslinked polyionic micelles system exhibits potential as a viable option for treatment of diabetes.