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In this chapter, we approach and examine the issue of innovation as applied to family and small and medium-sized enterprises (SMEs) in Cyprus, using, for research purposes, a structured questionnaire addressed to the particular type of business through mapping and grouping of the sample. The analysis concerns the periods 2015–2017, which are interesting due to the economic conditions that prevailed in the market in general. In this chapter, innovation is analyzed at both the policy level of the European Union and the institutional level. In particular, we examine the institutional dimensions of innovation in SMEs in Cyprus, such as, for example, the issue of financing, as well as the barriers often encountered by the companies in implementing innovative products, services or solutions. The chapter ends with interesting conclusions and an attempt to discuss future research extensions in the field of the institutional analysis of innovation.