The date pineapple (Ananas comosus var. comosus) was introduced to Hawaii is not known, but its presence was first recorded in 1813. When American missionaries first arrived in Hawaii in 1820, pineapple was found growing wild and in gardens and small plots. The pineapple canning industry began in Baltimore in the mid-1860s and used fruit imported from the Caribbean. The export-based Hawaii pineapple industry was developed by an entrepreneurial group of California migrants who arrived in Hawaii in 1898 and the well-connected James D. Dole who arrived in 1899. The first profitable lot of canned pineapples was produced by Dole’s Hawaiian Pineapple Company in 1903 and the industry grew rapidly from there. Difficulties encountered in production and processing as the industry grew included low yields resulting from severe iron chlorosis and the use of low plant populations, mealybug wilt that devastated whole fields, inadequate machinery that limited cannery capacity, and lack of or poorly developed markets for the industry’s canned fruit. The major production problems were solved by public- and industry-funded research and innovation in the field and in the cannery. An industry association and industry-funded cooperative marketing efforts, initially led by James Dole, helped to expand the market for canned pineapple. Industry innovations were many and included: selection of ‘Smooth Cayenne’ pineapple as the most productive cultivar with the best quality fruit for canning; identification of the cause of manganese-induced iron chlorosis and its control with biweekly iron sulphate sprays; the use of mulch paper and the mechanization of its application, which increased yields by more than 20 t·ha−1; and the invention of the Ginaca peeler–corer machine, which greatly sped cannery throughput. Nematodes were also a serious problem for the industry, which resulted in the discovery and development of nematicides in the 1930s. As a result, by 1930 Hawaii led the world in the production of canned pineapple and had the world’s largest canneries. Production and sale of canned pineapple fell sharply during the world depression that began in 1929. However, the formation of an industry cartel to control output and marketing of canned pineapple, aggressive industry-funded marketing programs, and rapid growth in the volume of canned juice after 1933 restored industry profitability. Although the industry supported the world’s largest pineapple breeding program from 1914 until 1986, no cultivars emerged that replaced ‘Smooth Cayenne’ for canning. The lack of success was attributed in part to the superiority of ‘Smooth Cayenne’ in the field and the cannery, but also to the difficulty in producing defect-free progeny from crosses between highly heterozygous parents that were self-incompatible. Production of canned pineapple peaked in 1957, but the stage was set for the decline of the Hawaii industry when Del Monte, one of Hawaii’s largest canners, established the Philippine Packing Corporation (PPC) in the Philippines in the 1930s. The expansion of the PPC after World War II, followed by the establishment of plantations and canneries by Castle and Cooke’s Dole division in the Philippines in 1964 and in Thailand in 1972, sped the decline. The decline occurred mainly because foreign-based canneries had labor costs approximately one-tenth those in Hawaii. As the Hawaii canneries closed, the industry gradually shifted to the production of fresh pineapples. During that transition, the pineapple breeding program of the Pineapple Research Institute of Hawaii produced the MD-2 pineapple cultivar, now the world’s pre-eminent fresh fruit cultivar. However, the first and major beneficiary of that cultivar was Costa Rica where Del Monte had established a fresh fruit plantation in the late 1970s. Dole Food Co. and Maui Gold Pineapple Co. continue to produce fresh pineapples in Hawaii, mostly for the local market. All of the canneries eventually closed, the last one on Maui in 2007.