One of the most consequential decisions in any enterprise cloud migration is deceptively simple to state and surprisingly hard to answer: do we move the workload as-is, or do we modernize it first?Having worked through cloud migrations across dozens of enterprise customers spanning both AWS and Azure. I can tell you this question rarely has a universal answer. The right path depends on the workload, the business context, and the maturity of the team inheriting it in the cloud. What follows is the decision framework I use when guiding customers through this choice.