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General William Tecumseh Sherman faced several challenges during his southern attacks, particularly during his famous "March to the Sea." He had to navigate difficult terrain, supply shortages, and the need for rapid movement to maintain the element of surprise. Additionally, he faced resistance from Confederate forces, which were often motivated and determined to defend their territory. Managing the logistics of his army while implementing a strategy of total war also posed significant challenges, as he aimed to undermine Confederate morale and infrastructure.

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