Cloud migration projects fail in the planning deck when teams treat them as pure infrastructure exercises. The successful ones map application dependencies, data gravity, and operational runbooks before anyone provisions a load balancer.
We sequence migrations in waves: non-critical services first, then stateful systems with rehearsed cutovers, then customer-facing paths with canary traffic and explicit rollback triggers. Each wave produces a post-mortem template—even when nothing goes wrong.
Database migration is usually the long pole. Read replicas, dual-write windows, and verification queries comparing row counts and checksums beat heroic weekend cutovers. Clients remember downtime; they rarely remember how elegant the Terraform was.
Observability must move with the workload. If metrics, logs, and alerts still point at the old environment after cutover, you have only migrated code—not operational responsibility.
The goal is not cloud for its own sake. It is elastic capacity, managed services that reduce toil, and security posture improvements your team can sustain. Measure success in deployment frequency and incident recovery time, not just monthly cloud spend.