While the area of organic crop production increases at a global scale, the potential interactions between pest management in organic and conventionally managed systems have so far received little attention. Here, we evaluate the landscape-level codependence of insecticide-based and natural enemy-based pest management using a simulation model for parasitoid-host interactions in landscapes consisting of conventionally and organically managed fields. In our simulations conventional management consists of broad-spectrum or selective insecticide application, while organic management involves no insecticides. Simulations indicate that insecticide use can easily result in lose-lose scenarios whereby both organically and conventionally managed fields suffer from increased pest loads as compared to a scenario where no insecticides are used, but that under some conditions insecticide use can be compatible with biocontrol. Simulations also suggest that the pathway to achieve the insecticide reduction without triggering additional pest pressure is not straightforward, because increasing the proportion of organically managed fields or reducing the spray frequency in conventional fields can potentially give rise to dramatic increases in pest load. The disruptive effect of insecticide use, however, can be mitigated by spatially clustering organic fields and using selective insecticides, although the effectiveness of this mitigation depends on the behavioral traits of the biocontrol agents. Poorly dispersing parasitoids and parasitoids with high attack rates required a lower amount of organically managed fields for effective pest suppression. Our findings show that the transition from a landscape dominated by conventionally managed crops to organic management has potential pitfalls; intermediate levels of organic management may lead to higher pest burdens than either low or high adoption of organic management.