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Pentland served in the fledgling Royal Australian Air Force (RAAF), and later the
Royal Air Force, before going into business in 1927. His ventures included
commercial flying around the goldfields of New Guinea, aircraft design and
manufacture, flight instruction, and charter work. In the early 1930s, he was
employed as a pilot with Australian National Airways, and also spent time as a
dairy farmer. Soon after the outbreak of World War II, he re-enlisted in the RAAF,
attaining the rank of squadron leader and commanding rescue and communications
units in the South West Pacific. Perhaps the oldest operational pilot in the
wartime RAAF, Pentland was responsible for rescuing airmen, soldiers and civilians,
and earned the Air Force Cross for his "outstanding courage, initiative and skill".
He became a trader in New Guinea when the war ended in 1945, and later a coffee