The second Jassy–Kishinev offensive, commonly referred to as the Jassy–Kishinev offensive named after the two major cities, Iași ("Jassy") and Chișinău ("Kishinev"), in the staging area, was a Soviet offensive against Axis forces, which took place in Eastern Romania from 20 to 29 August 1944 during World War II. The 2nd and 3rd Ukrainian Fronts of the Red Army engaged Army Group South Ukraine, which consisted of combined German and Romanian formations, in an operation to reoccupy Bessarabia and destroy the Axis forces in the region, opening the way into Romania and the Balkans.

The Kingdom of Romania, under the rule of King Carol II, was initially a neutral country in World War II. However, Fascist political forces, especially the Iron Guard, rose in popularity and power, urging an alliance with Nazi Germany and its allies. As the military fortunes of Romania's two main guarantors of territorial integrity—France and Britain—crumbled in the Fall of France, the government of Romania turned to Germany in hopes of a similar guarantee, unaware that Germany, in the supplementary protocol to the 1939 Molotov–Ribbentrop Pact, had already granted its blessing to Soviet claims on Romanian territory.