Estonians began leaving for the west at the start of the Second World War in 1939 and continued until the autumn of 1944, when the Soviet Union re-occupied Estonia. There are unconfirmed reports that some Estonians were able to flee in early 1945 as well. Fear of Soviet power and falling victim to repression were the main reasons for heading west. In addition to fleeing the Soviet occupation, other reasons for leaving were evacuation, recruitment of manpower, army recruitment, fleeing army recruitment, army mobilisation; and some were recruited to the police force, and withdrawn together with the army and wounded while transported to Germany.

From summer to autumn 1944, the great escape from Estonia happened mainly by cruise ship via the Port of Tallinn or along the north and western shoreline, as well as from the islands on boats. To a lesser extent, some headed west with planes and trains or by land with cars, bicycles, or horse drawn carriages. Attempts were also made on foot. Throughout the period of the war, close to 75,000 people fled to the west, and by the end of the war at least 40,000 of them were in Germany and more than 28,000 were in Sweden. During the first few months, 6–9% of those that fled Estonia died en route west.

Number of Estonians in the territories of Germany 1944/45: