This article is the first of our series on extending Microsoft AD CS beyond its design boundaries. Over the coming articles, we will cover topics including Linux certificate automation, DevOps and ACME pipeline integration, auto-enrollment at scale, IIS and web server certificate management, policy enforcement, and the operational case for professional Certificate Lifecycle Management. Each article focuses on a real use case drawn from community forums, GitHub projects, and conversations with IT teams who have faced these problems and built their own solutions to solve them. We will be honest about what those solutions achieve — and equally honest about where they reach their limits. If you manage certificates in a heterogeneous environment and have ever inherited various scripts, this series was written with you in mind.