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The friction characteristics of a shock absorber are very complex because the reciprocating motion is not always identical. In this study, a device was developed and used to analyze the dynamic friction characteristics under various reciprocating sliding conditions to determine the sliding materials and hydraulic oils that improve the shock absorber performance. This study describes the influence of hydraulic oil additive on the fine reciprocating friction characteristics of steel and copper alloy. Hydraulic oils were prepared by blending a paraffinic mineral oil with zinc dithiophosphate (ZnDTP) and polyhydric alcohol ester as additives. The results show that the dynamic frictional characteristics vary mainly depending on the additive concentration. A specific additive formulation induces a unique amplitude-dependent friction behavior. In addition, the influence of different additives on the lubrication mechanism is investigated based on the instrumental analysis of the friction surface.