The teenage Barry was educated with the prospect of becoming a tutor, but given a lack of evidence of any work history, the Bulkleys appear to have struggled to find Barry any suitable tutoring positions. A conspiracy appears to have developed between Barry, Mary-Ann Bulkley and some of the late James Barry's influential, liberal-minded friends (General Francisco de Miranda, Dr Edward Fryer, who had become Barry's personal tutor, and Daniel Reardon, the family's solicitor) to enable the teenage Barry to enter medical school. The University of Edinburgh was chosen and Mary-Ann and Barry boarded a Leith smack on 30 November 1809. And so, Margaret Anne Bulkley became James Barry, nephew of the late James Barry RA, and remained known thus for the next 56 years. In a letter to Daniel Readon, sent on 14 December, Barry asked for any letters addressed to Margaret Bulkley to be forwarded to Mary-Ann Bulkley (whom Barry now refers to as "my aunt"), and mentions that '...it was very usefull for Mrs. Bulkley (my aunt) to have a Gentleman to take care of her on Board Ship and to have one in a strange country...'. Although the letter was signed "James Barry", the solicitor indiscreetly wrote on the back of the envelope 'Miss Bulkley, 14 December'; this crucial piece of evidence was the one which enabled researchers to finally confirm that Margaret Bulkley and James Barry were one and the same.