cloudthinker-ai On-Premises to Cloud Migration Plan
Phase 1: Assessment & Discovery
- Inventory all on-premises assets
- Physical servers and specifications
- Virtual machines and hypervisor details
- Storage systems (SAN, NAS, local)
- Network topology and firewall rules
- Databases and data volumes
- Applications and their dependencies
- Classify workloads by migration complexity
- Identify licensing constraints (OS, database, middleware)
- Measure current performance baselines
Workload Classification Matrix
| Workload | Complexity | Data Volume | Downtime Tolerance | Migration Wave |
|---|---|---|---|---|
| Low/Med/High | GB/TB | Minutes/Hours/Days | 1/2/3/4 |
Phase 2: Network & Connectivity
- Design hybrid connectivity (VPN / Direct Connect / ExpressRoute)
- Plan IP address scheme for cloud environment
- Configure DNS resolution between on-prem and cloud
- Set up firewall rules and security groups
- Test bandwidth and latency between environments
Phase 3: Security & Compliance
- Map on-prem security controls to cloud equivalents
- Configure identity federation (AD/LDAP to cloud IAM)
- Set up encryption for data in transit and at rest
- Plan certificate migration or renewal
- Validate compliance requirements are met in cloud
Phase 4: Pilot Migration
- Select a low-risk, low-dependency workload
- Execute migration using chosen method (rehost/replatform)
- Validate functionality and performance
- Document lessons learned
- Refine migration playbook
Phase 5: Production Migration Waves
- Execute migrations in planned waves
- Run parallel environments during transition
- Validate data integrity after each wave
- Update DNS and routing progressively
- Monitor performance and error rates closely
Phase 6: Decommission & Optimize
- Verify all workloads running successfully in cloud
- Right-size cloud resources based on actual usage
- Implement cloud-native monitoring and alerting
- Decommission on-premises hardware
- Update disaster recovery and backup procedures
Counter-Rationalizations
| Shortcut | Counter | Why |
|---|---|---|
| "We can skip some steps for this case" | Adapt the workflow steps, don't skip them | Skipped steps are where incidents and oversights originate |
| "The user seems to already know what to do" | Complete all workflow phases with the user | The workflow catches blind spots that experience alone misses |
| "This is a minor case, full process is overkill" | Scale the process down, don't turn it off | Minor cases become major when unstructured; the process scales, not disappears |
| "I'll fill in the details later" | Complete each section before moving on | Deferred details are forgotten; real-time capture is more accurate |
| "The template output isn't necessary" | Always produce the structured output format | Structured output enables comparison, audit trails, and handoff to other teams |
Output Format
- Asset Inventory: Complete list of on-prem resources with cloud targets
- Migration Wave Plan: Grouped workloads with timelines per wave
- Network Architecture: Hybrid connectivity diagram
- Runbook per Wave: Step-by-step migration and rollback procedures
- Post-Migration Report: Performance comparison and optimization recommendations
Action Items
- Complete on-premises asset discovery
- Establish hybrid network connectivity
- Execute pilot migration and gather learnings
- Get change approval board sign-off for production waves
- Monitor each wave for 72 hours before proceeding
- Schedule datacenter decommission after final stabilization