Mosquitoes that carry Wolbachia endosymbionts may help control the spread of arboviral diseases, such as dengue, Zika and chikungunya. Wolbachia frequencies systematically increase only when the frequency-dependent advantage due to cytoplasmic incompatibility exceeds frequency-independent costs, which may be intrinsic to the Wolbachia and/or can be associated with the genetic background into which Wolbachia are introduced. Costs depend on field conditions such as the environmental pesticide load. Introduced mosquitoes need adequate protection against insecticides to ensure survival after release. We model how insecticide resistance of transinfected mosquitoes determines the success of local Wolbachia introductions and link our theoretical results to field data. Two Ae. aegypti laboratory strains carrying Wolbachia were released in an isolated district of Rio de Janeiro, Brazil: wMelBr (susceptible to pyrethroids) and wMelRio (resistant to pyrethroids). Our models elucidate why releases of the susceptible strain failed to result in Wolbachia establishment, while releases of the resistant strain led to Wolbachia transforming the native Ae. aegypti population. The results highlight the importance of matching insecticide resistance levels in release stocks to those in the target natural populations during Wolbachia deployment.