With the arrival of gunpowder in Europe in the 14th century, military practitioners were faced with a new challenge on the battlefield (though they initially tried to conceptualise the threat in old terms). They soon learned that gunpowder posed challenges for attacking the enemy as well as defending one's army or one's stronghold. This paper looks at this varied challenge through the lens of 'offense-defense theory', a product of modern political science and international relations, but rarely turned on much but the recent past. In particular this paper will look at the change in perception of what artillery was for in a siege situation and how both the attack and especially the defense changed in military strongholds in the late 15th through the 16th century.