In this video, we kick off a series of digital transformation horror stories with one of the most infamous failures in enterprise technology: the U.S. Air Force’s attempt to implement Oracle ERP across 200 legacy systems. Poor change management, over customization, weak governance, and a lack of unbiased requirements turned what should have been a $33 billion asset management solution into a decade-long nightmare. The lessons from this project are clear: without strong governance, risk assessment, and vendor independence, even the largest organizations can lose control of scope, budget, and outcomes.