Ryan and two accomplices were caught after a butcher shop robbery on 4 January 1964. He was charged with breaking and entering and theft offences on 6 January 1964. Bailed on 3 February 1964, Ryan skipped town and fled to New South Wales. He later admitted to nine robberies in New South Wales between 4 April and 11 July 1964. On a visit home on 14 July he was caught by Victoria Police in the early hours the next morning. On 13 November 1964 he received an eight-year prison sentence for breaking and entering. He was sent to Pentridge Prison.