An automated system and method for the online settling of a transaction is provided. The system comprises a server comprising a rules based engine including rules established on behalf of a party to the transaction and genetic programming logic configured to employ the rules and determine a plurality of transaction settlement offer sets, each transaction settlement offer set based on a set of circumstances and comprising multiple simultaneously presentable and individually selectable offers, each offer configured to provide an appearance of settling the transaction. The genetic programming logic creates a description of a current transaction settlement offer set, analyzes behavior and characteristics of the current transaction settlement offer set, establishes a fitness of the current transaction settlement offer set, and modifies the current transaction settlement offer set to produce a new transaction settlement offer set. The new transaction settlement offer set is provided to the user.