The 'Bombing of Tallinn', the Estonian capital, was undertaken first by the Germans within the context of their 'Barbarossa' attack on the USSR, and then by the Soviets as they drove the German forces back through the Baltic states toward East Prussia (1941/22 September 1944).

The first bombings by the Luftwaffe took place during the 'Summer War' of 1941, and a number of Soviet were later flown, between 1942 and 1944, against the city while it was occupied by the Germans.

When the USSR seized Lithuania, Latvia and Estonia in 1940, it gained control over a number of naval bases, including Tallinn, in the Baltic Sea, and even as 'Barbarossa' was characterised by the north-eastward advance of German land forces toward Leningrad, the Luftwaffe carried out several attacks on the Soviet-controlled naval bases. By August, the westernmost Soviet naval base was in Tallinn, and this made it a key target for German air attack. The Luftwaffe began to bomb Tallinn from the first days of the war in June 1941, and these attacks were intensified in August as the Soviets attempted to evacuate the city’s residents, elements of Vice Admiral Vladimir F. Tributs’s Baltic Fleet, formations of General Leytenant Piotr S. Pshennikov’s 8^th Army, and industrial assets important for war production. The Soviet forces lost control of Estonia in the summer of 1941, when the Germans began their occupation of the country.

German-occupied Tallinn was bombed by the Soviet air force on several occasions in May and September 1942. During the next year, more Soviet bombing missions on Tallinn followed in February, March, May, August, and September.

In February 1944, Germans began to use Tallinn for the storing of provisions, the establishment of supply depots and the basing of reserve units to support their front-line forces in Estonia. Tallinn’s harbour became a primary terminus for the German maritime transportation of equipment and other supplies for their forces on the northern and central parts of the Eastern Front. This increase of German activity in Tallinn inevitably caught the attention of the Soviets, who began to target the city in any effort to prevent, or at worst slow, the delivery of military necessaries to the German forces.

The most extensive and destructive of the Soviet air assaults was tat of 9/10 March 1944. A week before, the mayor of Tallinn had given an order that its population was to evacuate the town, but the evacuation failed and the destruction attendant on the resulting air attack was beyond the expectations of the people and the men of Heeresgruppe 'Nord'. The first attack, from 18.30 to 21.00, was delivered by 300 aircraft, which dropped 3,068 bombs, of which 1,725 were high explosive and 1,300 incendiary. Bombers struck Tallinn again at 02.00 for an additional 90 minutes. The local fire brigade service was short of water, as Soviet saboteurs had blown up the city’s pumping station before the air raid. A substantial portion of the suburbs, comprising large numbers of wooden buildings, went up in flames, and the city centre also suffered major damage. In all, about 20% of Tallinn’s buildings were burned to the ground. The military damage was minor as only a few military installations and supply stores were destroyed. The major military loss was the burning of 1 million litres (264,170 US gal) of fuel. Of the enterprises with some military importance, the Luther plywood factory and the cable factory run by Urania-Werke were destroyed. Most of the bombs fell on the homes and public buildings, including the Estonia theatre, St Nicholas church, the synagogue, four cinemas and the Tallinn city archives.

According to the official report, the death toll was 757 people, of whom 586 were civilians, 50 military personnel and 121 prisoners of war. Another 213 people had serious injuries, and 446 people minor injuries. Among the injured were 65 military servicemen and 75 prisoners of war. More victims were later found, with the number of deaths estimated at up to 800. More than 20,000 people were left without shelter in the spring thaw, while the military objectives were almost untouched. Immediately after the raid, Finnish bombers followed returning Soviet bombers to three air bases near Leningrad and bombed them. During the attack, about 25 Soviet aircraft were shot down over Tallinn, and 10 more succumbing to the Finns later in the same night.

Despite the high number of civilian casualties and low damage to military and strategic installations, sources disagree on whether or not the Soviet bombing raids were conducted primarily to destroy the morale of local civilians opposed to a return of Soviet occupation forces. Regardless of Soviet intentions, the raids' high civilian casualty toll significantly increased the hostility of the Estonian public toward the Soviets, already strong after 27 February, when a Soviet air raid had hit children playing in the school yard of Luunja, killing four children whose burial date became a national memorial day.

The last Soviet bombing raid on Tallinn was flown on the night of 21/22 September 1944.