In modern software development, maintaining accurate system documentation is a persistent challenge due to the complexity and dynamic nature of distributed systems. Traditional methods, such as manually created diagrams and documents, often become outdated quickly, leading to fragmented knowledge and inefficiencies. The reliance on manual updates introduces human error and fails to keep pace with continuous changes, making it difficult for developers to understand the system fully. To address these issues, automation emerges as a promising solution, with tools like OpenTelemetry and large language models (LLMs) offering potential to transform documentation processes. Multiplayer's approach leverages full stack session recordings and an automated system dashboard to provide real-time, accurate documentation that reflects how the system actually operates, thus enabling teams to debug, understand, and collaborate more effectively. This shift towards automated documentation not only preserves institutional knowledge but also empowers engineers to focus on building robust and maintainable systems.