By 1940, Deans was in the Middle East, where the 2NZEF had been transported for war service. He continued with his painting, doing landscapes of the Egypt countryside. His battalion commander, Lieutenant Colonel Howard Kippenberger, was supportive of his work. Deans later completed a portrait of Kippenberger which was used to illustrate his biography. In March 1941, the 2nd New Zealand Division was sent to Greece. The British Government anticipated an invasion of Greece by the Germans and decided to send troops to support the Greeks, who were already engaged against the Italians in Albania. The 2nd New Zealand Division was one of a number of Allied units dispatched to Greece. The campaign was little more than a series of withdrawals but Deans still found time to make depictions of life in the Greek villages he saw. At the end of the fighting in Greece, Deans was among those evacuated to Crete.