Predicting tableting performance of mixtures from that of individual components is of practical importance for achieving efficient and robust tablet design. It has been commonly assumed that a solid form exhibiting better tabletability will result in better tabletability when formulated. However, we show that the rank order of tabletability between two powders can flip when mixed with another powder, a phenomenon termed tabletability flip. Using three examples, we show that the tabletability flip upon mixing with microcrystalline cellulose is activated by the switch of the dominating factor in the bonding area (BA) and bonding strength (BS) interplay that determines tablet tensile strength. A mechanistic understanding of this phenomenon can significantly improve the accuracy of predicted tableting performance of mixtures from that of individual powders.