This thesis, relying on primary source documents and several secondary sources, addresses an important gap in the field of intelligence history. It is often thought that Soviet intelligence on German preparations to attack the USSR in June 1941 was excellent and pointed unambiguously toward the truth. In fact, this thesis demonstrates that while Soviet intelligence organizations before 22 June 1941 collected numerous signals of an impending German attack, the collective intelligence picture was muddled, conflicting, and often easy to discount. It analyzes the structures and processes of the Main Intelligence Directorate (GRU) of the Red Army, the People’s Commissariat for Internal Affairs (NKVD), and, from February 1941, the People’s Commissariat for State Security (NKGB) as independent entities that separately struggled to alert Soviet leadership of Operation Barbarossa. A plethora of reporting from the sources of all three organizations shows that the confusion evaporated by the beginning of June 1941. While intelligence from the GRU, NKVD and NKGB demonstrated that Germany was on the verge of invading, they failed to convince Stalin of its veracity. Even if they had done so, the warning was likely too late to react without Germany’s knowledge. By that point in the final weeks of peace, the Soviet Union was in the unfortunate position of being a victim of strategic surprise.