While From Russia With Love is certainly one of Ian Fleming's most discussed novels, little attention has been given to the influence of the earlier spy fiction pioneer Eric Ambler on the James Bond canon. This article exposes Fleming’s metatextual inclusion of Ambler's 1939 novel A Coffin for Dimitrios in the narrative of From Russia with Love as more than just Bond’s choice of reading. The text of A Coffin for Dimitrios forms the underlying foundation for historically relevant settings, themes, events, and characters, especially when observing Ambler's villain Dimitrios Makropoulos and his remarkable similarities to Fleming's Donovan "Red" Grant. As Ambler's novel actually saves Bond's life in his duel versus Grant, this warrants a closer look at the book's content, revealing in clear detail the dangers of time periods that are neither war nor peace and the enemies that operate within them; sadly, a distracted Bond never finishes the book, and thus fails to heed this warning. Gérard Genette's theory of hypertextuality, Hans Robert Jauss's concept of the "horizon of expectations", and Tzvetan Todorov's discussion of detective fiction genres each work in concert with this comparative analysis of the two novels, clarifying how Fleming not only transplants near-direct quotes out of and adopts elements from A Coffin for Dimitrios, but also updates, revises, and reinterprets them for the Cold War era.