System and Method for Generating Legal Documents

A system and method for the automated generation of documents for a legal transaction over a network using probabilistic prediction of customary usage. The predictions are generated by user experience, expert rules and machine learned classifiers based on user input of transaction data. The classifiers are constructed and tested on a partitioned dataset consisting of transaction data and legal document and clause selections in previous transactions. In one embodiment, such dataset is collected in a document management system.