This chapter examines the barriers to entrepreneurial internationalisation for creative and cultural industries from Ukrainian companies. It outlines the concepts of ‘creative economy’ and ‘creative industries’, which have rapidly gained importance in Ukraine. Their attractiveness is explained in part by their low capital requirements compared to traditional sectors. This creates low barriers to entry into the market and encourages start-ups. The sector’s national importance is such that Ukraine’s government investment agency profiles it as offering specific opportunities to build on the country’s expertise and desire for economic growth. In this chapter, the operationalisation of the creative economy in Ukraine is examined including the ‘direction of travel’ of its creative industries, which can be characterised around three related spatial themes: (1) regeneration initiatives, (2) IT hubs and (3) creative clusters. These themes provide the context for an exploration of the internationalisation processes for small and medium-sized enterprises (SMEs) in Ukraine. The internationalisation efforts and the strategies of small and micro-firms are analysed (Bayfield, Dana, and Stewart, 2009). The study of local creative SMEs illustrates the opportunities and challenges of internationalisation in the Ivano-Frankivsk region of Western Ukraine. With the help of the Ukrainian Chamber of Commerce and Industry, six case studies were conducted on local entrepreneurs that run internationally oriented businesses. Four of them are featured in this chapter. Despite the language challenges, it was found that there was a strong pull to internationalisation from not only bigger and wealthier markets but also from green and ethical consumers. Nevertheless, the case studies highlight the scope to develop the Ukrainian entrepreneurial ecosystem further to facilitate internationalisation.