Can established democracies nurture the establishment of democracies abroad? Should they do so? What issues – ethical, strategic, theoretical, operational, and diplomatic – accompany this exercise? What are the prospects for success? This chapter seeks to sketch out some tentative answers to these questions based mainly on the author's participation in, and observation of, the process by which established democracies – acting as nation-states or via surrogate organizations – currently seek to nurture democratic transitions worldwide, particularly in Africa. It is a process informed by social science, but not, on the whole, designed or implemented by scholars of democracy or transitions to democratic rule. It is also an exercise in which those responsible for arranging such assistance are “learning on the job” but have sought the advice of the social science community. In some cases, it has afforded a few individuals the opportunity to straddle, and in some instances join, two realms – the realm of the academic political scientist informed by the literature and one's own research in several countries emerging from authoritarian rule, and the realm of the policy maker, bureaucrat, and provider of assistance to support this process. As those who have previously straddled these realms know well, the interface between these two cultures is not always smooth nor does it necessarily result in more effective policy. Putting theory into practice is rarely automatic.