I recently cited Matthew Caffrey’s Toward a History-Based Doctrine for Wargaming, which is chock full of wargaming anecdotes, like this one on wargaming the Schlieffen plan:
The younger Moltke [the nephew of the great Moltke] started by going to the kaiser, a childhood friend (thanks to his famous uncle). He privately told the kaiser that the latter’s strategizing during the staff rides was closing off rigorous debate. The kaiser agreed to desist.Next, Moltke examined the wargames themselves. When he discovered that the effect of machine guns on the games was not being considered, he was told there was insufficient data to precisely predict their impact on attrition. Moltke saw to it that data acquired from the Russo-Japanese War could be used. He then asked why logistics were not being included. When told that wargames could not account for logistics, he pointed out that the Italian wargames had included logistics for decades.
Moltke then used his more objective and comprehensive wargame to test the Schlieffen plan. The game indicated that the two armies on the outside of the great wheel would run out of ammunition two days before the campaign ended. Moltke saw to it that Germany organized the first two motorized units of any army anywhere in the world — two ammunition supply battalions.