To elucidate deeper relationships within Rauvolfioideae (Apocynaceae), a phylogenetic analysis was conducted using sequences from five DNA regions of the chloroplast genome (matK, rbcL, rpl16 intron, rps16 intron, and 3′ trnK intron), as well as morphology. Bayesian and parsimony analyses were performed on sequences from 50 taxa of Rauvolfioideae and 16 taxa from Apocynoideae. Neither subfamily is monophyletic, Rauvolfioideae because it is a grade and Apocynoideae because the subfamilies Periplocoideae, Secamonoideae, and Asclepiadoideae nest within it. In addition, three of the nine currently recognized tribes of Rauvolfioideae (Alstonieae, Melodineae, and Vinceae) are polyphyletic. We discuss morphological characters and identify pervasive homoplasy, particularly among fruit and seed characters previously used to delimit tribes in Rauvolfioideae, as the major source of incongruence between traditional classifications and our phylogenetic results. Based on our phylogeny, simple style-heads, syncarpous ovaries, indehiscent fruits, and winged seeds have evolved in parallel numerous times. A revised classification is offered for the subfamily, its tribes, and inclusive genera.