We describe the lessons learned in deploying an intelligent trading agent for electronic Pay-Per-Click keyword auctions. Our discussion focuses upon the technical challenges in developing the bid management framework — an extensive internet communications infrastructure and database used to query market quotes, store data, and submit bids. In addition to the production system, we have also built an auction simulator for demonstration and testing purposes. The simulator allows the specification of a population of competitor bidding agents as tiny C# programs, which are dynamically compiled at runtime and run in the simulation. Through this simulator we present scenarios which demonstrate both the richness of our trading agent, and also some interesting scenarios in electronic auctions.