Mosquitos are among the deadliest insects on the planet due to their ability to transmit diseases like malaria through their bite. In order to bite, a mosquito must insert a set of micro-sized needles through the skin to reach vascular structures. The mosquito uses a combination of mechanisms including an insertion guide to enable it to bite and feed off of larger animals. Here, we report on a biomimetic strategy inspired by the mosquito insertion guide to enable the implantation of intracortical microelectrodes into the brain. Next generation microelectrode designs leveraging ultra-small dimensions and/or flexible materials offer the promise of increased performance, but present difficulties in reliable implantation. With the biomimetic guide in place, the rate of successful microprobe insertion increased from 37.5% to 100% due to the rise in the critical buckling force of the microprobes by 3.8-fold. The prototype guides presented here provide a reproducible method to augment the insertion of small, flexible devices into the brain. In the future, similar approaches may be considered and applied to the insertion of other difficult to implant medical devices.