This chapter addresses the primary difficulties that small and medium enterprises face when doing business online with international partners. The guidance provided in this chapter is primarily for owners of small and medium enterprises rather than legal for professionals. The two main problems inhibiting online transactions are a lack of trust between the parties and the risk inherent in the exchange. This chapter analyzes ways to address these problems. Many of the practical suggestions in this chapter are inspired not by million dollar deals but by playground transactions between children. Often the simple solutions are the best ones.