Lithium–sulfur (Li–S) batteries, due to the high theoretical energy density, are regarded as one of the most promising candidates for breaking the limitations of energy‐storage system based on Li‐ion batteries. Tremendous efforts have been made to meet the challenge of high‐performance Li–S batteries, in which a sulfur loading of above 5 mg cm−2 delivers an areal capacity higher than 5 mAh cm−2 without compromising specific capacity and cycling stability for practical applications. However, serious problems have been exposed during the scaling up of the sulfur loading. In this review, based on mechanistic insights into structural configuration, catalytic conversion, and interfacial engineering, the problems and corresponding strategies in the development of high‐loading Li–S batteries are highlighted and discussed, aiming at bridging the gap between fundamental research and practical cell‐level designs. Stemming from the current achievements, future directions targeting the high‐energy‐density Li–S batteries for commercialization are proposed. Challenges and corresponding strategies involving high‐loading lithium–sulfur batteries are comprehensively summarized and discussed based on shared mechanisms and concepts, from which perspectives and guidelines are provided for developing future strategies tackling intrinsic problems in high‐loading Li–S batteries.