A New Orleans jazz funeral begins in grief and ends in celebration, moving from a structured procession into joyful, improvised motion without anyone directing it. Dr. Tricia Diamond grew up inside that tradition; her father is interred in the Musicians' Tomb at St. Louis Cemetery No. 1. She is also a PhD aerospace engineer trained in failure mode analysis who directed a $386 million AI-integrated federal portfolio through real production failures under continuous audit. Using the four-stage structure of the jazz funeral as a working model, she walks through real AI failure scenarios and the architectural decisions, failure propagation boundaries, graceful degradation paths, and human recovery interfaces, that determined whether each one became a catastrophe or a footnote.