McIntyre left for Egypt on 12 January, intending to go onto to Italy where the 2nd New Zealand Division was engaged in the Italian campaign. However, while in Egypt he became ill with pneumonia and had to be hospitalised. It was not until March 1944 that McIntyre headed for Cassino, where the division was involved in heavy fighting. Some of his most notable war art was produced at this time, including depictions of the controversial bombing of the Cassino Monastery. He was in Rome shortly after the city's liberation by American forces, where at Freyberg's request he executed a portrait of Pope Pius XII. For most of the remainder of the war he followed the 2nd New Zealand Division as it advanced up Italy.