There is approximately a half century of published research on harvest mechanization of cultivars of Capsicum annuum var. annuum L. This review focuses primarily on research pertaining to chile for canning and fresh markets. Most of the crop is still harvested by hand, displacing production to locations where labor costs are low. Mechanizing chile harvest will require a systems approach, integrating research in plant breeding, production practices, and harvester and processing plant machinery design. Cultivars need to be selected for high determinant fruit set, low attachment force, and increased fruit wall toughness. Production practices need to be modified to cause the development of tall, well-rooted plants with minimal branching. Harvest machinery needs to be developed that is both aggressive enough to remove almost all fruit and gentle enough to minimize damage. Processing plant equipment needs to be developed to handle fruit that may have more foreign matter, some stems still attached, and will arrive in large batches. A fully mechanized harvest will not be possible until each part of the system is in place.