In 1814 he fell into trouble, "aiding and abetting", in an attempted escape from Van Diemen's Land to South America, seven transported convicts; Antonio Martinio, Forteso De Santo, Patrick McCabe, Vissanso Boucherie, Antonio Janio, Montrose Johnson and William Green. The group secretly went to Recherche Bay to fell trees with which they built a lugger. When the lugger was completed, Fawkner was put ashore and made his way back to his farm. After sailing some distance out into the open ocean, the remaining men on the lugger returned to Van Diemen's Land because of leaks in the water tanks. The vessel was sighted at the entrance to the Derwent by a government ship, and taken in charge because of her 'singular appearance'. Fawkner and Santos were the only ones of the group tried and in August 1814 were each sentenced to 500 lashes and three years hard labour. In a letter dated 19 October 1814 from Lieut.-governor Davey to Lieutenant Jeffreys instructs him that he is to receive on board John Fawkner: Fawkner's account of this incident was that "a party of prisoners, determined to escape, sought his assistance and that in a moment of foolish sympathy he undertook to help them". He wrote the following account of the incident later in life: