This chapter provides an insight into how real life IT projects happen in investment banks. Each case study is a true account based on the actual experiences of the author. The first case study is regarding bonds. It is taken from a project to build a fixed income (bond) platform for the middle office in the UK division of a large Dutch bank called Rabobank. The project became known as RABOND. The second is on front office foreign exchange. It is taken from a project to build an exotic currency options pricing and risk management system for the front office of NatWest Markets in the mid‐1990s. The project was known as EcoRisk. The third study is on equity confirmations project. It is taken from a project to build a confirmations system for the operations department of equity derivatives within the investment bank SBC Warburg (now part of UBS).