Howe arrived in Hobart on October on the convict ship "Indefatigable". He was sent to work for John Ingle, who had once been the Supervisor of Convicts. He was now a farmer and merchant. Howe soon escaped and went into the bush. He joined up with a large group of escaped convicts who had become bushrangers (robbers). The gang of 28 was led by John Whitehead. It included two soldiers (who had deserted) and two aboriginal women.