Most cloud migration checklists assume you're starting clean. In practice, you're migrating a decade of accumulated cron jobs, undocumented integrations and one server nobody wants to touch.
Before you migrate anything
- Inventory every workload, including the ones nobody remembers building.
- Classify each by data sensitivity — this determines your compliance posture before it determines your architecture.
- Identify hard dependencies between systems; these dictate migration order, not convenience.
Sequencing the cutover
Migrate stateless services first. They're reversible if something goes wrong. Save anything holding transactional data for last, after your rollback plan has been tested against a lower-stakes migration.
The cost trap
Lift-and-shift migrations routinely come in 30-40% more expensive than the on-prem baseline in month one, because nobody right-sized the instances. Budget a right-sizing pass at 60 and 90 days post-migration, not just at go-live.
Our Cloud Migration team has run this playbook across Healthcare, FinTech and Travel workloads — happy to sanity-check your migration plan.