In regulated markets companies must comply with various rules, standards, and approval protocols to avoid expensive lack-of-compliance costs. Such regulations often limit the ability of companies to advertise and thereby reach out to consumers. This paper uses a qualitative multiple case-study approach to explore, from an industry perspective, how three different companies (a whisky producer, a microbrewery, and an alcohol importer) use digital advertising to raise brand awareness on the Swedish alcohol market. The firms are relatively similar in their approaches, unanimously preferring the use of social media advertising and conducting all activities through the lens of the regulations. However, the degree to which the firms are willing to take risks and find innovative solutions to the unique problems inherent to the regulated market in question differs. Although the study is context-specific, previous research has suggested that features and market practices in one regulated market can influence another. This thesis contributes to the literature on the broader topic of advertising on regulated markets, where research is primarily written from a public health perspective.