Questions about the story's accuracy are not new. In a newspaper article in The Scotsman, "Greyfriars Bobby A Dog's Devotion" (11 August 1934), Councillor Wilson McLaren responds to contemporary questions about the accuracy of the stories by describing his own conversation, in 1871, with "Mr Traill" of "Traill's Coffee House" in relation to the dog he himself was then feeding, reassuring readers about the story Mr Traill had given him, and describing responses in 1889 to questions about the story's accuracy. A sense of the difficulty of determining accuracy is gained from two opposing letters to The Scotsman newspaper on 8 February 1889 (part of the debate referred to by McLaren), both from people claiming close links to Greyfriars Kirk, both claiming to have known of the dog personally but with opposing views over the accuracy of stories.
Fleming was a heavy smoker and drinker throughout his adult life and suffered from heart disease. In 1961, aged 53, he suffered a heart attack and struggled to recuperate. On 11 August 1964, while staying at a hotel in Canterbury, Fleming went to the Royal St George's Golf Club for lunch and later dined at his hotel with friends.