Dr James Barry, a surgeon in the British Army from 1813 until his retirement in 1859, became famous after his death following the revelation that he was in fact a woman who had masqueraded as a man for no less than 56 years. This paper reviews Margaret Bulkley’s student years at the University of Edinburgh from the time of her adoption of the identity of the youth calling himself James Barry. The deception was perpetrated in order to obtain a medical degree and the three year MD curriculum was completed without discovery. Few facts are known about these years (1809–1812) and the work of Lisa Rosner has been invaluable as a source of prosopographical information to apply to our knowledge of James Barry’s experiences during his time at Edinburgh. Contemporary letters and an Army document also assist in developing this unique and extraordinary story, revealing much that was previously unknown as well as some data, which in earlier work were incorrectly reported.