This article examines the bombing of Tallinn on the evening of 9 March 1944 and on the night before 10 March by the Soviet long-range air force (ADD) using ADD documents. Red Army offensives were in progress in the directions of Narva, Pskov, and Ostrov at the time of the bombing of Tallinn. For this reason, the bombing can be placed in the context of supporting those offensives. According to ADD documents, Tallinn was treated as a transportation junction and supply base for the German forces. The city’s industry was considered to be in operation in the interests of German war objectives. Most ADD units were assigned the port or the railway junction (Baltic Railway Station) as their targets in Tallinn. The city centre in general was assigned as the target of one ADD division. Its mission was to destroy military-industrial objects but its orders did not specify the objects. The precision of ADD bombing was already poor due to the fact alone that they were operating in darkness and the bombs were dropped from a great height. It follows that in parallel with the specification of bombing the port and railway junction, the Soviets counted on the random dropping of bombs over the city centre and on bombs that fell off target from the port and the railway junction (such a result was inevitable due to the general imprecision of bombing) in regard to the remaining military-industrial objects. According to ADD headquarters, a total of 659 aircraft flights to Tallinn were executed in two waves. The mission was registered as having been completed in 624 of those flights. A total of 5,640 bombs were dropped with a total weight of 816.42 tonnes. The ADD’s losses were small: 11 aircraft went missing in action, 10 aircraft suffered serious damage from enemy fire and three of them made emergency landings. The Finnish air force attacks on three ADD airfields near Leningrad on the evening of 9 March did not affect the ADD’s activity in bombing Tallinn. The ADD already planned to bomb Tallinn again on the following night, but that attack was postponed each subsequent day due to unfavourable weather conditions over the course of the following weeks in March until the plan was finally abandoned.