Lockheed U-2 Dragon Lady reconnaissance aircraft became famous overnight in May of 1960 when one of these planes was shot down near Sverdlovsk (now Ekaterinburg). This incident put an end to flights over Soviet territory, and later imagery intelligence (IMINT) missions were carried out by satellites. From an Estonian point of view, the interesting question of whether and to what extent U-2s were used for missions over Estonian territory, which was then occupied by the Soviet Union, has never been dealt with in historiography. This article gives a definitive answer based on declassified CIA documents. It appears that in the period 1956-1958, U-2s flew over Estonia rather frequently. For this period, there are 75 CIA IMINT reports dealing with objects located in different parts of Estonia – ports, airfields, military bases and production facilities. For 1959 and the first four months of 1960, there is no data but it is logical to assume that the flights conducted in this period also covered some Estonian territory. The exact dates and routes of missions remain classified. However, since different objects were photographed during each individual mission, this number is lower than the overall number of reports. Therefore, the number of flights had to be several dozens.