This text is fundamentally built upon the diplomatic correspondence held between the State Department and the US Embassy in Madrid during the second half of the 40s (preserved at the National Archives Records Administration (NARA). Our attention has been focused on this rich and abundant material with the aim of highlighting how emphatically was reiterated the proposition in American political channels that refraining from carrying out threatening (let alone punitive) actions against Francoist Spain was the best formula, if not the only one, to produce favourable conditions for a transition from Dictatorship to Democracy in the country. Even though each one through their own lenses and personal outlook, both Carlton J.H. Hayes and Norman Armour, as well as William W. Butterworth, Philip W. Bonsal and Paul T. Culbertson (successively heading the American Mission at the time) reached the conclusion that good doses of pragmatism, flexibility and perseverance were required to successfully face the Spanish question. Only by doing this, they thought, the conditions the country needed to overcome its deep-rooted social and historical contradictions and shortcomings might be met.