By approaching the phenomenon of structural ambiguity from two different perspectives – psycholinguistic and computational, this thesis shows how linguistic research can have practical applications in improving NLP systems. The analyses of specific sentences show breakdowns in processing, present the possible explanations for the reasons behind them through principles such as Minimal Attachment/Late closure and Lexical preference, and demonstrate the backtracking needed in order to achieve a full, successful parsing of ambiguous sentences. The types of sentences chosen for this thesis are called garden-path sentences, which induce a lot of difficulty in processing for both humans and machines, making them a perfect choice to demonstrate the...