In summer 1943, Taylor was deployed to Cairo to gather watercraft for the unit's upcoming missions in the Aegean Sea. Taylor was active before the Battle of Leros, dodging German troops and carrying supplies to MI6 operatives. He often collaborated with American film actor Sterling Hayden, who worked for the OSS Special Operations branch. In September 1943, Taylor was appointed OSS Operations Officer in Italy, where he set up a Maritime Unit branch in the city of Bari to supply Josip Broz Tito's Yugoslav Partisans, a guerilla force fighting against Nazi Germany in occupied Yugoslavia. After the December 1943 air raid on Bari, Taylor relocated the OSS base of operations to Monopoli. Taylor personally led many of the Maritime Unit's covert missions, including one into Albania to rescue a flight of American nurses and medics who had been forced down in the Ceraunian Mountains. On a later trip, Taylor and his men were trapped in Albania for three months, sneaking back into Italy in July 1944 with letters from Albanian nationalist Abaz Kupi.