cloudthinker-ai Cloud Migration Assessment Skill
Assess cloud migration readiness for {{ project_name }} targeting {{ target_cloud }}.
Workflow
Step 1 — Portfolio Discovery
Build an application inventory:
APPLICATION PORTFOLIO
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
Total applications: {{ application_count | "TBD" }}
| App Name | Owner | Tech Stack | Criticality | Current Host | Users |
|----------|-------|-----------|-------------|-------------|-------|
| [app] | [team] | [lang/framework] | CRITICAL/HIGH/MED/LOW | [DC/colo] | [count] |
For each application, capture:
[ ] Application name and business function
[ ] Owning team and technical contact
[ ] Technology stack (language, framework, runtime)
[ ] Business criticality tier
[ ] Current hosting (data center, colo, on-prem)
[ ] Dependencies (upstream and downstream)
[ ] Data sensitivity (PII, PHI, PCI, public)
[ ] Compliance requirements (SOC2, HIPAA, PCI, GDPR)
[ ] Current infrastructure cost (monthly)
[ ] Licensing constraints (tied to hardware, cores, etc.)
Step 2 — 6R Strategy Classification
Classify each application using the 6R model:
6R CLASSIFICATION
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
REHOST (Lift and Shift):
Criteria: No code changes, move as-is to cloud VMs
Best for: Legacy apps with tight timelines
Apps: [list]
REPLATFORM (Lift and Reshape):
Criteria: Minor optimizations (managed DB, containers)
Best for: Apps that benefit from managed services with minimal changes
Apps: [list]
REPURCHASE (Replace with SaaS):
Criteria: Replace with commercial SaaS product
Best for: Commodity workloads (email, CRM, HR)
Apps: [list]
REFACTOR (Re-architect):
Criteria: Significant redesign for cloud-native
Best for: Strategic apps that need scalability/resilience
Apps: [list]
RETAIN (Keep on-premises):
Criteria: Cannot move due to latency, compliance, or cost
Best for: Mainframes, hardware-dependent, regulatory restrictions
Apps: [list]
RETIRE (Decommission):
Criteria: No longer needed, redundant, or replaced
Best for: Legacy apps with no active users
Apps: [list]
SUMMARY:
| Strategy | Count | % of Portfolio |
|----------|-------|---------------|
| Rehost | ___ | ___% |
| Replatform | ___ | ___% |
| Repurchase | ___ | ___% |
| Refactor | ___ | ___% |
| Retain | ___ | ___% |
| Retire | ___ | ___% |
Step 3 — Dependency Mapping
DEPENDENCY ANALYSIS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] Application dependency graph created
[ ] Shared databases identified (multi-app databases)
[ ] Shared services identified (auth, logging, messaging)
[ ] External integrations documented (APIs, file transfers)
[ ] Network dependencies mapped (latency-sensitive connections)
[ ] Data gravity analysis (where is the data, what depends on it)
MIGRATION BLOCKERS:
| Blocker | Affected Apps | Mitigation | Owner |
|---------|--------------|------------|-------|
| [blocker] | [apps] | [mitigation] | [name] |
Step 4 — Wave Planning
MIGRATION WAVES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
Wave 0 — Foundation (Month 1-2):
[ ] Landing zone / account structure
[ ] Networking (VPC, VPN/Direct Connect, DNS)
[ ] Identity (SSO, IAM, RBAC)
[ ] Security baseline (GuardDuty, Config, CloudTrail)
[ ] Monitoring and logging infrastructure
Wave 1 — Quick Wins (Month 2-3):
[ ] Low-risk, low-dependency applications
[ ] Development/staging environments
[ ] Internal tools and utilities
Apps: [list]
Wave 2 — Core Services (Month 3-5):
[ ] Shared services and platforms
[ ] Databases and data stores
[ ] Medium-criticality applications
Apps: [list]
Wave 3 — Critical Workloads (Month 5-7):
[ ] Production customer-facing applications
[ ] High-criticality tier-1 services
[ ] Data-intensive workloads
Apps: [list]
Wave 4 — Cleanup (Month 7-9):
[ ] Remaining applications
[ ] Legacy migrations requiring refactoring
[ ] Data center decommissioning
Apps: [list]
Step 5 — Risk Assessment
RISK REGISTER
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| Risk | Likelihood | Impact | Mitigation | Owner |
|------|-----------|--------|------------|-------|
| Extended downtime during migration | MED | HIGH | Blue-green cutover | [name] |
| Data loss during transfer | LOW | CRITICAL | Checksums + dry run | [name] |
| Performance degradation in cloud | MED | HIGH | Load test pre-cutover | [name] |
| Cost overrun | HIGH | MED | FinOps review per wave | [name] |
| Skills gap | MED | MED | Training + partner support | [name] |
| Compliance violation | LOW | CRITICAL | Pre-migration audit | [name] |
| Vendor lock-in | MED | MED | Multi-cloud abstractions | [name] |
Step 6 — Cost Model
COST COMPARISON
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
| Category | Current (Monthly) | Cloud (Monthly) | Delta |
|----------|------------------|-----------------|-------|
| Compute | $___ | $___ | ___% |
| Storage | $___ | $___ | ___% |
| Network | $___ | $___ | ___% |
| Database | $___ | $___ | ___% |
| Licensing | $___ | $___ | ___% |
| Operations/staff | $___ | $___ | ___% |
| **Total** | **$___** | **$___** | **___%** |
Migration one-time costs: $___
Payback period: ___ months
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
Produce a migration assessment report with:
- Portfolio summary with application inventory and 6R classification
- Dependency map with migration blockers identified
- Wave plan with timeline and application assignments
- Risk register with mitigations
- Cost model with current vs cloud comparison
- Recommendations and next steps