A company attempted a large-scale DevOps initiative to improve their development and production processes, but faced many challenges that ultimately led to failures in production. The company cultures and teams were spread across geographies and silos, leading to tension when a new elite team was brought in. Technical debt from 10 environments and long stage gates caused knowledge vacuums and splits between new and experienced employees. Key lessons included needing more empathy, data-driven decisions, treating DevOps as an organizational change, and ensuring production-like environments in development to prevent failures in production.