A variety of methods including penetrating enhancers, enzyme inhibitors, as well as cargo mediated drug delivery have been explored to improve the intolerance of parenteral administrated insulin, but little success has been achieved so far. Under this background, cell penetrating peptides (CPPs), with their ability to enhance transport efficiency of macromolecular drugs have been demonstrated to be able to increase insulin bioavailability (BA) in a number of studies, of which a BA up to 50.7% relative to subcutaneously administered insulin could be achieved by nasal route under optimal conditions. Furthermore, CPPs could be conveniently formulated with insulin, or be grafted onto drug-loaded cargoes to facilitate the cargo mediated insulin delivery. Here we reviewed the recent achievements on CPP-mediated insulin transport, and outlined various CPP-based delivery strategies which are expected to show potential in clinical translation in the future.