Abstract: The friction properties of a dilute solution of block copolymer additives in poly-α-olefin (PAO) confined between mica surfaces were investigated using the surface forces apparatus. Friction measurements were made for poly(11-acrylamidoundecanoic acid)-block-poly(alkyl methacrylate)-block-poly(11-acrylamidoundecanoic acid) with an alkyl chain length of C12 (A5L946A5) in the poly(alkyl methacrylate) blocks. The results were compared to those for a PAO solution of a similar triblock copolymer with an alkyl chain length of C18 (A5S992A5) examined in our previous work (Yamada et al., Langmuir 2015). The friction coefficient μ for A5L946A5/PAO was approximately 0.5, which was one or two orders of magnitude larger than that for A5S992A5/PAO (μ of 0.002–0.039). Detailed analysis of the dynamic thickness and contact geometry enabled us to investigate the difference in the friction reduction abilities of the two additives. A5L946A5 has a high affinity to PAO and the molecules have expanded conformation in PAO; extensive chain entanglement effect results in the formation of a thick and viscous lubricant layer, which gives rise to high friction. On the other hand, A5S992A5 has low affinity to PAO, and the shrunken A5S992A5 molecules adsorbed on the surfaces form a rigid slip plane at the interface, which gives rise to low friction. Our results provide insights into the oil/additive combinations used for low friction in oil-based lubrication.