Cloud migrations rarely fail because of the cloud. They fail because of what wasn't planned for before the migration started. Here's a practical checklist based on patterns we see across enterprise migrations.
Start with a full inventory of what you're actually moving — applications, dependencies, data volumes, and integration points. Migrations that skip this step routinely discover hidden dependencies mid-project.
Classify workloads by migration strategy: some applications can be rehosted as-is, others need to be re-platformed to take advantage of managed services, and a smaller set genuinely needs to be rearchitected. Treating every workload the same way wastes time and money in both directions.
Plan data migration and cutover separately from application migration. Data gravity is real — moving terabytes of data takes time and bandwidth planning that's easy to underestimate.
Build cost governance in from day one. Cloud's pay-as-you-go model can just as easily balloon costs as reduce them without tagging, budgets, and alerts in place from the start.
Finally, plan your security and compliance posture for the cloud environment specifically — identity and access management, encryption, and audit logging all work differently than in an on-premises environment, and retrofitting them after go-live is far more expensive than designing them in from the start.