The phrase “cloud-native” has become overrated in today’s tech scene. Every familiar enterprise technology product is now rebranded as “cloud-native” and is offered as a containerized workload for today’s business needs. But are they really “cloud-native” ? To answer this question we have to deeply understand the cloud native qualities. Can our existing enterprise monoliths become cloud native or use cloud native tools ? is it worthwhile to break down the monolith as today’s advice goes ? This deck focuses on those hard questions in today’s enterprise landscape. This is a discussion with enterprise architects on the challenges they face in their cloud native journey.