Craig arrived in Sydney in January 1812 on the Guildford (the same ship which conveyed Walter Preston the engraver to the colony). He had previously been sentenced to seven yearstransportation at Middlesex Jail Delivery for anunspecified crime. On 10 August he received a ticket of leave but thirteen months later he absconded but was soon captured and sent to Van Diemen’s Land. In August 1814, while on his way to Hobart fromLaunceston under guard, Craig and the three other prisoners were ‘rescued’ by the infamous Michael Howe and his gang of bushrangers. When he realized that the bushrangers planned to revenge themselves upon the two soldiers who had been charged with escorting him to Hobart, Craig freed these men and accompanied them to Hobart. Theauthorities rewarded him by allowing him to paint and providing him with paper and drawing materials.