Pollination is critical for the production of many crops, and both insect- and wind-based pollination systems are increasingly disrupted by bloom asynchrony, weather events, and high demand for available insect pollinators. Artificial pollination systems can provide a security of yield even in poor pollination scenarios, and have been attracting increasing attention over the past decade. Here, we review pollen collection and pollen application technologies that have been employed to date. Major categories of mechanical pollination technology include: hand-pollination, handheld and backpack devices, vehicle-mounted devices, unmanned aerial vehicles (UAVs), and robotic and autonomous pollinators. The majority of the artificial pollination systems above are used to supplement natural pollination, but for some crops, these systems were found to perform adequately by themselves, including kiwifruit, olive, date palm, walnut, tomato, and hybrid maize seed. These systems often treat pollen as a system input, creating a chicken-and-egg problem in which the system is not economical without pollen and the pollen is not economical to collect without wide uptake of the system. To combat this, there has been success in developing mechanical harvesters for some crop plants (particularly almond and maize), but future work is needed for artificial pollination to be a commercial reality for the increasing number of cropping systems that are experiencing pollination deficits.