The games include a scenario editor, and much of the content in the follow-up games are designs developed by the community of avid players. The maximum number of in-game events is 500 (or 1,000 for TOAW III version). The variability of these events makes each scenario-when properly designed-very complex and variable.

The game also includes 'events', which is a series of programmable events which display a message and can have several different causes and effects. Each unit is assigned unique equipment (types of infantry, tanks, aircraft, etc.) and given its own name, info and color code. The maximum number of units that can be made in a scenario was 2,000 per side until TOAW IV, although managing more than 200 can often be complicated. The option of scale is left to a maker of a particular scenario to choose, resulting in a wide range of user-made scenarios ranging from, for example, a small engagement in northern Germany between several companies to an entire World War II on division scale. The scale of the game is variable, with distances ranging from 2.5 km per hex to 50 km per hex, and each turn simulating from 1/4 day to 1 week of time, but is fundamentally 'operational', focusing on battalion, division, and corps combat. The basic appearance of the game is the traditional view onto a hexagonal grid, although the player may choose a map-like overhead view with military symbols and basic info for the units, or an isometric view that depicts the units with small pictures of soldiers, tanks, etc. The Operational Art of War: Century of Warfare (2000).

The Operational Art of War II: Elite Edition (2000).The Operational Art of War II: Flashpoint Kosovo (1999).The Operational Art of War II: Modern Battles 1956–2000 (1999).

The Operational Art of War III