This chapter explains the development of an app that is designed to assist micro-entities to address commercial contract legal risk. Micro-entities are the smallest of small enterprises. The impetus to undertake the production of this artefact stems from the need to address the lack of available legal risk management (LRM) advice tools for them. Micro-entities have significant problems when dealing with trading problems arising from the purchase or sale of goods or services between an individual and the business or with another business and constitute more than half the legal problems they face. It is in this spirit that Online Legal Risk Advisory Service (OLRAS) was developed. It follows the lines of a 1980s legal expert system using Prolog and “if-then” rules. Some preliminary insights which need to be confirmed by beta testing indicate the potential of OLRAS to be used as a tool that micro-entities can use to “lawyer up” against larger organisations with sophisticated legal functions. Once this further work is done, OLRAS could assist micro-entities in engaging in self-evaluation of their legal risk exposure in the context of negotiating commercial contracts for the purchase or sale of goods and/or services. As micro-entities cannot afford legal advice and usually enter into commercial agreements with larger enterprises without the benefit of LRM guidance, an app that can help closing this e-justice gap cannot come too soon.