Negative entropy has been known in Casimir systems for some time. For example, it can occur between parallel metallic plates modeled by a realistic Drude permittivity. Less well known is that negative entropy can occur purely geometrically, say between a perfectly conducting sphere and a conducting plate. The latter effect is most pronounced in the dipole approximation, which occurs when the size of the sphere is small compared to the separation between the sphere and the plate. Therefore, here we examine cases where negative entropy can occur between two electrically and magnetically polarizable nanoparticles or atoms, which need not be isotropic, and between such a small object and a conducting plate. Negative entropy can occur even between two perfectly conducting spheres, between two electrically polarizable nano-particles if there is sufficient anisotropy, between a perfectly conducting sphere and a Drude sphere,and between a sufficiently anisotropic electrically polarizable nano-particle and a transverse magnetic conducting plate.