At the age of 16 d'Arry Osborn left Princes to help his father Francis Ernest Osborn (PAC 1904-1908) run the family winery d'Arenberg, which was established on the family property in McLaren Vale in 1912. In 1957 d'Arry assumed full management of the business and 2 years later bottled the first wines to carry the famous red striped label.
During the 1960s d'Arry's wines were recognised. His 1969 Cabernet Sauvignon won the coveted Jimmy Watson Trophy and a Grenache-based wine collected 7 trophies and 29 gold medals from capital city wine shows. With these successes came national and international recognition, and in 1999 d'Arenberg was recognised as one of the world's top 70 wineries.
Shortly after celebrating his 50th consecutive vintage at d'Arenberg in 1994, d'Arry was made a Patron of the Australian Wine Industry. Rowen Osborn (PAC 1940-1942) is a part-owner of the business, and d’Arry’s son Chester (PAC 1975-1979) has been chief winemaker since 1984 and is the fourth generation in the business