Migration Readiness Assessment

Step 1: Gather context

Ask the user:

> What workload are you planning to migrate? Please share: > - Workload name and code packages/directories to analyze > - Current environment (on-premises, other cloud, colocation) > - Business drivers (cost, agility, compliance, end-of-life hardware, etc.) > - Timeline constraints (optional)

If context is already provided or you are in a codebase, proceed directly.

Step 2: Application Stack Discovery

Analyze the codebase to understand the current application stack.

You MUST examine:

• Programming languages and runtimes (versions, compatibility with AWS services)
• Frameworks and libraries (web frameworks, ORM, messaging)
• Database technologies (relational, NoSQL, search, caching)
• Middleware and message brokers
• External service dependencies (APIs, SaaS integrations)
• Configuration management (config files, environment variables, secrets)
• Operating system dependencies and system-level requirements
• Build and packaging systems (Maven, npm, pip, Docker)

For each component, document:

• File path and line numbers
• Technology and version
• AWS equivalent or migration path
• Migration complexity (simple lift, requires changes, requires rewrite)
• Dependencies on other components

You MUST flag as BLOCKER:

• OS-specific dependencies without cloud equivalents
• Proprietary software with licensing restrictions (Oracle, specific Windows features)
• Hardware-specific dependencies (FPGA, specific CPU instructions, USB dongles)
• Hardcoded IP addresses or hostnames in application code
• Local filesystem dependencies (shared network drives, local storage)

Step 3: Infrastructure Discovery

Analyze existing infrastructure configurations.

You MUST examine:

• Server configurations (CPU, memory, storage requirements)
• Network topology (VLANs, firewalls, load balancers, DNS)
• Storage systems (SAN, NAS, local disk, file shares)
• Database configurations (engine, version, size, replication)
• Monitoring and alerting systems
• Backup and DR configurations
• Security controls (firewalls, IDS/IPS, WAF, certificates)
• Existing IaC if any (Terraform, Ansible, Chef, Puppet)

For each infrastructure component, document:

• Current configuration
• AWS equivalent service
• Migration approach (rehost, replatform, refactor)
• Data volume and transfer considerations

Step 4: Dependency Mapping

Map all internal and external dependencies.

You MUST examine:

• Service-to-service communication (protocols, ports, patterns)
• Database connections (connection strings, pooling, multiple consumers)
• Shared databases or data stores (multiple services writing/reading)
• External API integrations (third-party services, partner APIs)
• Network dependencies (latency-sensitive connections, VPN tunnels)
• Batch job dependencies (scheduling, order of execution)
• Authentication/authorization dependencies (LDAP, AD, SSO)

You MUST create a dependency diagram showing:

• All services and their connections
• Data flows and protocols
• External dependencies
• Migration wave groupings (what must move together)

You MUST flag as HIGH RISK:

• Tight coupling between components that must move together (increases blast radius)
• Shared databases accessed by multiple services (migration ordering constraint)
• Latency-sensitive integrations that will span hybrid during migration
• Hard dependencies on on-premises systems that cannot move (require hybrid connectivity)

---STOP--- Checkpoint: Discovery and dependency mapping complete — ready to determine migration strategy

> Mapped the application stack ({X} components), infrastructure configurations, and dependency relationships. Identified {Y} blockers, {Z} high-risk dependencies (shared databases, latency-sensitive integrations), and migration wave groupings. > > Shall I proceed with determining the migration strategy (7 Rs) for each component and assessing readiness by pillar?

Do NOT proceed past this point until the user explicitly confirms.

Step 5: Determine migration strategy (7 Rs)

For each component, evaluate which strategy fits based on code evidence:

| Strategy | When to use | Code Indicators | |----------|-------------|-----------------| | Rehost | Fast migration, minimal changes | Standard OS, containerizable, no OS-specific deps | | Replatform | Small optimizations during move | Self-managed DB → RDS, self-managed cache → ElastiCache | | Refactor | Need cloud-native benefits | Monolith that should be decomposed, stateful → stateless | | Repurchase | Replace with SaaS | Commercial software with AWS/SaaS equivalent | | Retire | No longer needed | Unused code, deprecated services | | Retain | Not ready to move | Hard dependencies, compliance blockers | | Relocate | VMware workloads | VMware-specific configurations |

You MUST justify each recommendation with code evidence.

Step 6: Assess readiness by pillar

For each pillar, provide: Readiness (Ready/Conditionally Ready/Not Ready), Evidence (file:line), Gaps, Actions needed.

Operational Excellence Readiness

• Is there IaC? (CloudFormation, Terraform, CDK, Ansible)
• Are CI/CD pipelines in place? Can they target AWS?
• Is monitoring portable or tied to specific tools?
• Are operational procedures documented?

Security Readiness

• Are there compliance requirements affecting region/service choice?
• How are secrets managed? (hardcoded, vault, config files)
• Are there network security dependencies needing equivalents?
• Is identity management compatible with AWS IAM/Identity Center?

Reliability Readiness

• What is the current availability? What's the target?
• Are there HA mechanisms to replicate?
• What's the acceptable downtime during migration?
• Are backup/recovery procedures tested?

Performance Efficiency Readiness

• Are there latency-sensitive integrations?
• Are there hardware-specific dependencies?
• What are current performance baselines?
• Are there SLAs to maintain during cutover?

Cost Optimization Readiness

• What's the current TCO? (hardware, licensing, ops, facilities)
• Are there licensing implications? (BYOL, license-included, re-purchase)
• Are there existing contracts or prepaid commitments?

Sustainability Readiness

• Can migration reduce resource footprint?
• Are there opportunities for Graviton/serverless?
• Can managed services replace self-managed infrastructure?

Step 7: Risk Assessment

For each risk, assess using Impact × Likelihood:

Impact: Minor (schedule slip, minor rework) | Moderate (significant rework, extended hybrid period) | Severe (migration failure, data loss, extended outage)

Likelihood: Low (unlikely with proper planning) | Medium (possible without specific mitigation) | High (likely given current state)

| Impact | Likelihood | Risk Level | |----------|------------|------------| | Severe | High | Critical | | Severe | Medium | High | | Severe | Low | High | | Moderate | High | High | | Moderate | Medium | Medium | | Moderate | Low | Medium | | Minor | High | Medium | | Minor | Medium | Low | | Minor | Low | Low |

---STOP--- Checkpoint: Risk assessment complete — ready to produce the final migration assessment

> Assessed {N} risks across the migration. Risk distribution: {X} Critical, {Y} High, {Z} Medium, {W} Low. Overall readiness: {Ready / Conditionally Ready / Not Ready}. Critical blockers and mitigations identified. > > Shall I produce the full Migration Readiness assessment with migration plan and cost comparison?

Do NOT proceed past this point until the user explicitly confirms.

Step 8: Produce the assessment

markdown
# Migration Readiness Assessment: {Workload Name}

## Executive Summary
- **Date**: {date}
- **Packages Analyzed**: {list}
- **Recommended Strategy**: {primary strategy}
- **Overall Readiness**: {Ready / Conditionally Ready / Not Ready}
- **Estimated Effort**: {T-shirt size with justification}
- **Key Risks**: {top 3}
- **Critical Blockers**: {count and brief description}

## Application Stack Summary
| Component | Technology | Version | AWS Equivalent | Strategy | Complexity |
|-----------|-----------|---------|---------------|----------|------------|
| {name} | {tech} | {ver} | {aws service} | {7R} | {Low/Med/High} |

## Dependency Map
{PlantUML diagram showing service dependencies, data flows, and migration wave groupings}

## Readiness Scorecard
| Pillar | Readiness | Score (1-5) | Key Blocker | Action Needed |
|--------|-----------|-------------|-------------|---------------|
| Operational Excellence | {status} | {score} | {blocker} | {action} |
| Security | {status} | {score} | {blocker} | {action} |
| Reliability | {status} | {score} | {blocker} | {action} |
| Performance Efficiency | {status} | {score} | {blocker} | {action} |
| Cost Optimization | {status} | {score} | {blocker} | {action} |
| Sustainability | {status} | {score} | {blocker} | {action} |

## Critical Blockers
{For each: ID, description, evidence (file:line), impact on migration, resolution approach, effort}

## Risks and Mitigations
| Risk | Evidence | Risk Level | Migration Impact | Mitigation | AWS Service |
|------|----------|------------|-----------------|------------|-------------|
| {risk} | {file:line} | {level} | {impact} | {mitigation} | {service} |

## Pre-Migration Checklist
{Ordered by priority — what must be done before migration starts}
- [ ] {action with evidence of why it's needed}

## Migration Plan

### Phase 1: Mobilize (Weeks 1-2)
| Task | Dependencies | AWS Service | Evidence |
|------|-------------|-------------|----------|
{Landing zone, connectivity, tooling setup}

### Phase 2: Migrate (Weeks 3-6)
| Wave | Components | Strategy | Data Volume | Downtime Window |
|------|-----------|----------|-------------|-----------------|
{Component migration waves based on dependency analysis}

### Phase 3: Optimize (Weeks 7-8)
| Optimization | Component | Expected Benefit | AWS Service |
|-------------|-----------|-----------------|-------------|
{Right-sizing, managed services, serverless, Graviton}

## AWS Services for Migration
| Category | Service | Purpose | Relevant Components |
|----------|---------|---------|-------------------|
| Server | AWS MGN | Rehost EC2 | {components} |
| Database | AWS DMS | Replicate with minimal downtime | {components} |
| Data | DataSync / Snowball | Large-scale transfer | {components} |
| Schema | AWS SCT | Schema conversion | {components} |
| Network | Direct Connect / VPN | Hybrid connectivity | {components} |
| Governance | Control Tower | Multi-account | All |

## Cost Comparison
| Category | Current (monthly est.) | AWS Estimated | Delta | Notes |
|----------|----------------------|---------------|-------|-------|
| Compute | {estimate} | {estimate} | {delta} | {basis} |
| Storage | {estimate} | {estimate} | {delta} | {basis} |
| Networking | {estimate} | {estimate} | {delta} | {basis} |
| Licensing | {estimate} | {estimate} | {delta} | {basis} |
| Operations | {estimate} | {estimate} | {delta} | {basis} |

## Next Steps
{Top 5 concrete actions the team should take this week to prepare}

Step 9: Offer follow-up

After delivering the assessment, offer:

> Would you like me to: > - Design the AWS landing zone architecture? > - Create a detailed data migration plan for a specific database? > - Estimate AWS costs in detail for specific components? > - Build a pre-migration testing strategy? > - Design the hybrid connectivity architecture? > - Create IaC for the target AWS architecture?

Calibration Guidance

• A workload already containerized with CI/CD and IaC is LARGELY READY — focus on AWS-specific optimizations and data migration planning
• Every blocker and risk MUST have code evidence — don't flag "licensing risk" without checking actual dependencies
• Migration strategy recommendations must be justified by code analysis (not assumptions)
• "Cannot Determine" is valid for runtime characteristics not visible in code (e.g., actual data volumes, network latency requirements)
• For shared databases, always flag the migration ordering constraint — this is the #1 cause of migration complexity
• Cost estimates from static analysis are rough — acknowledge uncertainty and recommend AWS Pricing Calculator for precision
• Acknowledge migration-ready aspects prominently (containerized, stateless, IaC already exists)