Protective covers (i.e., glasshouses, netting enclosures, and polytunnels) are increasingly used in crop production to enhance crop quality, yield, and production efficiency. However, many protected crops require insect pollinators to achieve optimal pollination and there is no consensus about how best to manage pollinators and crop pollination in these environments. We conducted a systematic literature review to synthesize knowledge about the effect of protective covers on pollinator health and pollination services and identified 290 relevant studies. Bees were the dominant taxon used in protected systems (90%), represented by eusocial bees (e.g., bumblebees (Bombus spp.), honey bees (Apis spp.), stingless bees (Apidae: Meliponini)), and solitary bees (e.g., Amegilla spp., Megachile spp., and Osmia spp.). Flies represented 9% of taxa and included Calliphoridae, Muscidae, and Syrphidae. The remaining 1% of taxa was represented by Lepidoptera and Coleoptera. Of the studies that assessed pollination services, 96% indicate that pollinators were active on the crop and/or their visits resulted in improved fruit production compared with flowers not visited by insects (i.e., insect visits prevented, or flowers were self- or mechanically pollinated). Only 20% of studies evaluated pollinator health. Some taxa, such as mason or leafcutter bees, and bumblebees can function well in covered environments, but the effect of covers on pollinator health was negative in over 50% of the studies in which health was assessed. Negative effects included decreased reproduction, adult mortality, reduced forager activity, and increased disease prevalence. These effects may have occurred as a result of changes in temperature/humidity, light quality/quantity, pesticide exposure, and/or reduced access to food resources. Strategies reported to successfully enhance pollinator health and efficiency in covered systems include careful selection of beehive location to reduce heat stress and improve dispersal through the crop; increased floral diversity; deploying appropriate numbers of pollinators; and manipulation of flower physiology to increase attractiveness to pollinating insects. To improve and safeguard crop yields in pollinator-dependent protected cropping systems, practitioners need to ensure that the delivery of crop pollination services is compatible with suitable conditions for pollinator health.