In this paper, we offer broad insight into the underperformance of Arabic constituency parsing by analyzing the interplay of linguistic phenomena, annotation choices, and model design. First, we identify sources of syntactic ambiguity understudied in the existing parsing literature. Second, we show that although the Penn Arabic Treebank is similar to other treebanks in gross statistical terms, annotation consistency remains problematic. Third, we develop a human interpretable grammar that is competitive with a latent variable PCFG. Fourth, we show how to build better models for three different parsers. Finally, we show that in application settings, the absence of gold segmentation lowers parsing performance by 2–5 % F1. 1