Austin Kinnane, my great grandfather, four generations back, was a free settler to New South Wales, Australia. Immigrating with his wife and young family from Ireland, they undertook a journey that began as a dream, and ended as a nightmare. Austin would find himself a convicted convict, serving time in the worst places Cockatoo Island, Norfolk Island and finally Van Dieman’s Land. The essay shares his story drawing upon convict records, genealogical records and historical research.