With the Germans entering the Estonian capital Tallinn, Soviet “Red Banner” Baltic Fleet leaves port, heading 200 miles East through Gulf of Finland for Kronstadt near Leningrad. 200 vessels carrying Soviet 10th Rifle Corps sail in 7 groups starting at 11.18 AM. The main battlefleet with cruiser Kirov, under the command of Vice-Admiral Vladimir Tributs, is the last to depart at 2.52 PM. German Ju88 bombers attack immediately. At 4 PM, Soviet ships become trapped in German/Finnish minefields off Cape Juminda, under aerial bombing plus shellfire from the Estonian shore, and at dusk they are attacked by German & Finnish torpedo boats. A total of 15 warships and submarines and 15 transports ships are sunk (12,000 lives lost). Soviet ships anchor overnight, unable to proceed through the minefield.
In the Ukraine, NKVD blow Zaporozhye hydroelectric dam on the River Dnieper to prevent its use by the Germans. People downstream are not warned and thousands are killed in the torrent. Germans will rebuild part of the dam and restore power generation.
The new Iranian government of Mohammad Ali Foroughi signs a treaty allowing the Britain and USSR to protect oil fields and the Trans-Iranian Railway; however, troops are not allowed in the capital Tehran. In addition, German, Italian, Hungarian and Romanian legations are to be closed and all remaining German nationals handed over to the Allies.
130 miles West of Crete, Greece, British Submarine HMS Rorqual sinks Italian steamer Cilicia. Rorqual is rammed by escort torpedo boat Antares, sustaining damage to her periscope. U-101 and U-558 attack convoy OS-4 330 miles West of Ireland. U-558 sinks British MV Otaio (13 dead and 58 survivors picked up by destroyer HMS Vanoc). U-101 is chased away by a destroyer which drops 30 depth charges over 3 hours causing minimal damage.