Failing to achieve cultural understanding has shown to be counterproductive to the success of military operations. Past military operations have resulted in failure or experienced difficulties due to the neglect of cultural understandings of the local populace. As technology and tactics change the cultural understanding of people remain as an important objective to achieve success. Understanding the results of past operations can assist in increased awareness and training to improve the military for success in future situations. Examples of past failures during armed military operations in Cuba and the Philippines will be compared to the successes during recent operations in Iraq.