PentagonOs Urban COIN Wargame (1966) - John Curry - Bog

This is an example of an early professional counter insurgency game written for the Pentagon to explore an urban uprising.
It is a multi-player megagame representing a growing urban crisis. The government have their police and the general support of the population. The key is to position the guards at the threatened critical urban infrastructure to increase the chance of detecting bomb threats. They also use their secret police to uncover the insurgents.

The players representing the public have roles from factory owners to middle class shop-keepers. They have to maintain their income, in the face the growing insurgent threat. Their support decides who wins the game.

The insurgents have sway the population, but also disrupt the cities economy. Of course, they can only do this if they remain undiscovered.

Included are detailed player briefings, after action reviews, along with analysis of 20 key uprisings.

This book is published by the History of Wargaming Project.