Resistance against the Soviets continued in the Moonsund Archipelago until November 23, 1944, when the Germans evacuated the Sõrve Peninsula.
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As a consequence to the German occupation of Estonia during World War II (1941–1944) and fleeing the Soviet occupation of Estonia (1944), Ole left as a refugee to Finland in 1943, where he continued to paint portraits of personalities of Finnish cultural life, such as the ones of the linguist Lauri Kettunen and of Viljo Tarkiainen, biographer of Aleksis Kivi, and landscapes.
From 1942 to 1944, during the German occupation, he studied at the Tartu University's Faculty of Law, also being a member of the Estonian Students' Society.