A modern tech stack is filled with choices; as the tech market has exploded over the last ten years; there are solutions for nearly every conceivable problem. Software as a Service is now commonplace amongst companies large and small. With so many options to choose from, it's easy to make bad choices that could haunt you for years or even centuries. A company called Cloudsmith made such a choice in 2016 when they selected Chef over Puppet for configuration management, and later opted for Chef Provisioning instead of Hashicorp's Terraform for Infrastructure as Code. However, Terraform continued to improve while Chef Provisioning became outdated, causing Cloudsmith significant issues that ultimately led them to switch to Terraform after a month-long engineering hiatus. The experience serves as a cautionary tale about the importance of choosing wisely when evaluating tools and technologies.