In this work we learn clusters of contextual annotations for non-terminals in the Penn Treebank. Perhaps the best way to think about this problem is to contrast our work with that of<cite> Klein and Manning (2003)</cite> . That research used treetransformations to create various grammars with different contextual annotations on the non-terminals. These grammars were then used in conjunction with a CKY parser. The authors explored the space of different annotation combinations by hand. Here we try to automate the process -to learn the "right" combination automatically. Our results are not quite as good as those carefully created by hand, but they are close (84.8 vs 85.7).