This paper is an interpretive multiple case study of corporate social initiatives in Latvia. A country that just over a decade ago began its journey of recovery from 50+ years of occupation by the Soviet Union, Latvia has undergone social, economic, and judicial changes to reclaim its position in the global community of democratic nations. Among those changes is the emergence of a burgeoning non-profit sector that contributes to the development of civil society. As Latvia's economy stabilizes, companies are increasingly engaging in philanthropic activities. While corporate and social sector collaboration is a growing trend in Latvia, it is still not widely understood or applied to its full potential. There is broad interest in encouraging the development of corporate social responsibility (CSR) in Latvia. This set of case studies describes five examples of corporate and social collaboration in more detail and offers a brief analysis as to the strengths and weaknesses of each. Each case represents one example of five types of corporate social initiatives as defined by authors Kotler and Lee in their book, "Corporate Social Responsibility: Doing the Most Good for Your Company and Your Cause". The paper's main research question is: What motivates a business in Latvia to seek a partnership with the social sector and how are obstacles overcome in order to achieve effective collaboration? The case studies and subsequent conclusions and recommendations create a snapshot of corporate social initiatives in Latvia today, and may encourage businesses and non-profit organizations in Latvia to see beyond the limitations and obstacles that are generally assumed as justification not to take action.