This chapter considers the way in which regimes of extraterritoriality were experienced and enacted by early trading companies, such as the Dutch East India Company (VOC), the English East India Company, and the Levant Company. It focuses on its dual role as both privilege and punishment, and the shifting connotations with which it was imbued – initially bestowed as a privilege by a dominant host ruler on foreign traders, extraterritoriality also served as a symbol of shame when imposed upon host nations. The chapter discusses recurrent conditions of rupture within host state legal systems when engaging with extraterritoriality. It argues that the exercise of extraterritoriality in the varied contexts of the major trading companies occupied specific spaces and was reflective of the inconsistent, ‘messy’, uneven, and often improvised nature of informal empire. VOC policies on law reflected the need to adapt to local conditions, but were utilised throughout its operations as another mode of empire.