In early June I. and III./JG 77 were deployed to Romania and subordinated to IV. "Fliegerkorps" under the command of Kurt Pflugbeil. The battle group was designated as close air support to Army Group South. On 22 June 1941 the German Wehrmacht commenced Operation Barbarossa, the invasion of the Soviet Union. Freytag achieved steady success. He reported his 10th claim on 12 August 1941 and his 20th victory on 31 October 1941. This day he downed a Mikoyan-Gurevich MiG-3 in the morning during a combat air patrol to support German forces in the Battle of Rostov. Aleksandr Grosul and Ivan Voytenko of the 55 IAP were reported missing in action. On 23 March 1942, Freytag engaged and shot down a Yakovlev Yak-1. The "Staffel" engaged three Yak-1s from the 247 IAP this day, piloted by Major Mikhail Fedoseyev, the unit commander, Stepan Karnach, Vasiliy Shevchuk and Viktor Golovko. Fedoseyev was killed while Shevchuk was shot down and force-landed. One of the Yak fighters became Freytag's 26th victory. II./JG 77 also took a heavy toll of Soviet air forces in the Siege of Odessa, before Freytag's group was withdrawn to Kherson. In the autumn, 1941, JG 77 was heavily involved in operations over the Crimea. In December the Red Army made an amphibious assault on the eastern end of the region to disrupt the Siege of Sevastopol and re-establish airbases there. Throughout December 1941 and through to June 1942, north I. and II./JG 77 were involved in combat operations (III./JG 77 was removed because of losses). Kerch fell to the Axis on 20 May 1942. Freytag's II "Gruppe" (group) participated in the Sevastopol operation with III. "Gruppe" until mid-June.