Simulating upcoming operations has been a key aspect of the German military planning process for generations. They conducted wargames at every echelon to test an operation's hypothesis, investigate alternate courses of action, speculate on possible enemy reactions, etc. Barbarossa was no exception. Among the best-known wargames were those of the Army High Command (OKH), held in the autumn of 1940. After the publication of official directives and orders, the following winter the army groups, armies, and corps conducted their own simulations. This article examines two operational-level wargames conducted in February and March 1941 for Army Groups North and South. It discusses the set-up, conduct, and subsequent analysis of each, with further investigation into how actual operations differed from the simulations. Significantly, both wargames ignored the initial frontier battles, and began 7–10 days into the campaign, while both assumed Barbarossa would begin in the second half of May. Army Group South conducted Planspiel 'Otto' at its headquarters in France from 20 January to 5 February. A Planspiel was a certain type of simulation where staff brainstormed the plan, rather than 'played' a wargame. The Sixth, Seventeenth, Twelfth Armies, and First Panzer Group participated, often with Army Group Commander Field Marshal Gerd von Rundstedt in attendance. Army Group South was initially very spread out, with the Panzer group especially lacking mass. Describing Otto's conclusion, the army group chief of staff highlighted the location of the main effort, army-Luftwaffe cooperation, flank security, and the roles of allies, among other topics. Second Army conducted a Kriegsspiel of Army Group North's operations at Munich, between 10-13 March. A Kriegsspiel replicates actual operations, as played by Red (German) and Blue (Soviet) teams. Army Commander, Colonel General Maximilian Freiherr von Weichs oversaw the simulation, but unlike Rundstedt, Army Group North Commander Field Marshal Wilhelm Freiherr von Leeb did not attend. Reflecting OKH Chief of Staff Colonel General Franz Halder's emphasis on taking Moscow, Army Group North, particularly its panzer group, concentrated on securing the left flank of Army Group Center. It did not treat attacking Leningrad or crossing the lower Dvina River as important. Neither wargame bore much resemblance to Barbarossa's actual operations. In the Balkans, Operations Marita and 25 (invasions of Greece and Yugoslavia, respectively) dramatically changed Army Group South's landscape. In the Baltic States, independent thrusting operations toward Leningrad became the new main effort of Army Group North. This article sheds light on the planning and execution of the campaign on its two flanks. [ABSTRACT FROM AUTHOR]