In this paper, we focus on the verb-particle (V-Prt) split construction in English and German and its difficulty for parsing and Machine Translation (MT). For German, we use an existing test suite of V-Prt split constructions, while for English, we build a new and comparable test suite from raw data. These two data sets are then used to perform an analysis of errors in dependency parsing, word-level alignment and MT, which arise from the discontinuous order in V-Prt split constructions. In the automatic alignments of parallel corpora, most of the particles align to NULL. These mis-alignments and the inability of phrase-based MT system to recover discontinuous phrases result in low quality translations of V-Prt split constructions both in English and German. However, our results show that the V-Prt split phrases are correctly parsed in 90% of cases, suggesting that syntactic-based MT should perform better on these constructions. We evaluate a syntactic-based MT system on German and compare its performance to the phrase-based system.