The purpose of our case study is to understand how a change request comes about, as well as the steps that are taken to implement it. Change requests are key elements of software maintenance and evolution. They may be small or large, depending on the needs of the organisation. To deal with change requests, the project manager and project team members have a dedicated plan to follow; it is called a change request management plan. The aim of this case study is to illustrate how a change request is put forward, as well as the ensuing implications. Our case study is based on the following scenario: Max, the narrator, is a junior project manager at IngeniousTec, which is a website software, digital services, and marketing provider for the automotive industry. Working closely with the project managers and stakeholders enabled Max to take meticulous note of how the corporation operates. In this chapter, he highlights his experiences working on two projects in which change requests played a major role, but were handled differently. This resulted in one project being considered a phenomenal success and the other a complete disaster from a project management’s perspective.