Convergent evolution is a major topic in evolutionary biology. Low bone cortical compactness (CC, a measure of porosity of cortical bone) in the extant genera of “tree sloths,” has been linked to their convergent slow arboreal ecology. This proposed relationship of low CC with a slow arboreal lifestyle suggests potential convergent evolution of this trait in other slow arboreal mammals. Femoral and humeral CC were analyzed in “tree sloths,” lorisids, koala, and extinct palaeopropithecids and Megaladapis, in comparison to closely related but ecologically distinct taxa, in a phylogenetic framework. Low CC in “tree sloths” is unparalleled by any analyzed clade and the high CC in extinct sloths suggests the recent convergence of low CC in “tree sloths.” A tendency for low CC was found in Palaeopropithecus and Megaladapis. However, lorisids and the koala yielded unexpected CC patterns, preventing the recognition of a straightforward convergence of low CC in slow arboreal mammals. This study uncovers a complex relationship between CC and convergent evolution of slow arboreality, highlighting the multifactorial specificity of bone microstructure.