Throughout the early modern period, significant commercial links existed between the Shetland Islands and the cities of Bremen and Hamburg. These links, which predominantly evolved around the export of whitefish and herring from Shetland, have received some scholarly attention in the past. However, older research tends to reduce the commercial exchange to a simple bilateral affair and to marginalize the involvement of Scottish merchants. This article aims to address some of these misconceptions by highlighting the complexity of Shetland-German trade relations. In particular, the article analyzes the significance of territories bordering the cities of Bremen and Hamburg, the participation of Scottish traders, and the use of Scandinavian flags of convenience. In doing so, it offers a fresh perspective on Shetland's commercial exchange, based on old and new sources maintained in German and Scottish archives.