This essay outlines some of the benefits and challenges of implementing strategic knowledge management systems in small and medium-sized enterprises (SMEs) with reference to respective initiatives in the Republic of Singapore. The article addresses following research questions: What is knowledge management (KM) and why has it become an issue? How can SMEs benefit from strategic KM? What are the potential pitfalls of KM applications in small firms? What are the strategic imperatives of using KM in SMEs? Do small and large firms require different KM systems? What are the critical success factors which have to be considered during implementation? How do smart and KM-enabled SMEs look in reality? Some of these issues will be illustrated by a case-study of a small intelligent pest control firm in Singapore whose owners made effective use of development grants provided by government agencies tasked with the transformation of Singapore's small business sector in line with official IT-related development blueprints. Since the 1980s, the Government of this dynamic city-state in Southeast Asia has implemented several policy measures to realize the vision of an "intelligent island" aimed at remaining relevant in the global knowledge-based economy.