This chapter is dedicated to the work of the theater director, writer, and critic Cipriano de Rivas Cherif (1891–1967) during the Spanish Civil War. While his contributions to theater in the 1920s and 1930s have largely been reviewed—he decisively shaped the image of the modern theater director in Spain—his activity as a diplomat in the service of the Second Spanish Republic is a less prominent aspect of his multi-layered oeuvre that still awaits closer examination, especially from the perspective of his own literary involvement in this period. This chapter examines the two-act play ¿Qué quiere decir Irene? (What does Irene mean?, 1941), first published in 2013 and performed as a staged reading in Madrid in 2019, as the work that most poignantly reflects Rivas Cherif’s experiences as Consul General and Secretary of the Spanish Delegation to the League of Nations in Geneva (1936–1938). Like his entire literary oeuvre of the post-war period, it has so far attracted little scholarly interest-unjustly so: the drama offers insights from an unusual perspective into the fault lines within the Republican faction and can be read as an outsider’s astute commentary on the failure of diplomacy in 1930s Europe.