Word order optionality in the postfinite domain in North and Continental West Germanic has attracted much attention in generative syntax in the past three decades, in particular the phenomena known as ‘Object Shift’ and ‘Scrambling’. However, the precise factors conditioning this word order optionality remain unclear, and there is to date no account which can explain the full cross-Germanic variation on display. This project will shed new light on this area via novel data from Middle Low German (1200-1650) and historical Icelandic (1150-2008), which are well placed to fill gaps in the literature on the topic and are accessible for this type of study via parsed corpora (Corpus of Historical Low German; Icelandic Parsed Historical Corpus). In particular, the factors of case and head-directionality will be investigated, as well as information-structural and semantic factors, all of which have been shown to be relevant for individual languages. In order to achieve this, a new annotation scheme which encodes the relevant information-structural and semantic properties will be developed as a generally applicable enhancement for historical Penn-style treebanks and will be employed for the two corpora in use. Additionally, the project will develop a novel way to measure and model gradience in word order flexibility within the architecture of Lexical-Functional Grammar in order to facilitate comparison between the Low German and Icelandic data and with further Germanic varieties.