In 1961, Hughes was one of the twelve companies that submitted proposals to meet U.S. Army TS-153 requirement for a four-seat turbine-powered light observation helicopter. Model 369 was developed and flew first on 27 February 1963. Five machines of this type were ordered as OH-6A for the evaluation programme. The OH-6A Cayuse powered by an Allison T63-A-5A turboshaft was the winner of the U.S. Army's contest in May 1965. Deliveries commenced in September 1966 to meet an initial three-year commitment for 1071 machines. Next to the military OH-6A Hughes developed a larger, five-passenger civilian version. Initially designated as the 369H and 369A during the development stage, it emerged on the market as the Hughes 500. In 1968, the 500C with the more powerful Allison 250-C20 engine was introduced. In 1977, the 500D entered the market with a new five-bladed rotor system and the Allison 250-C20B engine. In 1982, Hughes introduced both the 500E with the Allison 250-C20B and the 530F with the more powerful Allison 250-C30 engine. On 6 January 1984, Hughes Helicopters became a subsidiary of McDonnell Douglas, and subsequently re-designated the McDonnell Douglas Helicopter Company. The Hughes 500 thus became the MD500.

Hughes 369D N369HL came in for fuel at the Heli-Holland heliport near Emmen in the Netherlands. The 1980-built Hughes 369D c/n 1170220D was registered first N58169 and N644WA in the US. On 30 April 2004, the Hughes 500 was registered G-CCUN in the UK with London Air. The G-CCUN was registered with Heli Logistics at Sywell on 2 November 2006 and the registration was cancelled as exported to the USA on 10 July 2007. The aircraft was not exported but was registered N369HL in the US with Southern Aircraft Consultancy Inc. Trustee, Cornwall, UK, on 16 July 2007. The Hughes 369D is still active in the London aerea.

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