Barr tried to escape from his confinement four times. By November 1942 he had recovered sufficiently from the injuries he received in June to break out of the hospital where he was being held in Bergamo, northern Italy. He made his way to the Swiss border, but was challenged by an Italian customs official, whom he struck with a rock before being recaptured. Court-martialled on a charge of murder, he only avoided a death sentence when the Swiss Red Cross colonel representing him located the official and proved that he had not died. Barr was instead sentenced to ninety days solitary confinement in Gavi Prison Camp, Genoa. In August 1943, with Italy on the verge of surrender, prisoners of war were rounded up for transport to Germany. Barr jumped from a moving train bound for the Brenner Pass and joined a group of Italian partisans in Pontremoli, remaining at large for two months before again being captured. Taken to a transit camp just over the Austrian border, Barr and fourteen other prisoners escaped by tunnelling under the barbed wire. Eventually he managed to link up with an Allied special operations unit, which was gathering intelligence behind enemy lines, sabotaging Axis infrastructure, and helping Allied prisoners and Italian refugees escape over the Apennine Mountains along the so-called "Alpine Route". He was recaptured and escaped once more before finally making it through the Alpine crossing himself, leading a group of more than twenty. After reaching friendly lines in March 1944, he was sent to a military hospital in Vasto, weighing only and in poor health, suffering malaria, malnutrition, and blood poisoning. The assistance he rendered to fellow Allied fugitives earned him the Military Cross (MC) for "Exceptional courage in organising escapes"; the award was gazetted on 1 December 1944. He is thought to be one of only five or six RAAF pilots to receive the MC during World War II.