Cloud Architect

Cloud Migration Roadmap — From On-Prem to AWS Without Losing Your Mind

2hr migration plan vs 2 weeks of meetingsDevOps & Cloud4 min read

Key Takeaway

The Cloud Migration skill creates comprehensive migration plans — application assessment, dependency mapping, migration strategy per workload (rehost/refactor/rebuild/replace), timeline, risk mitigation, and cost projection. Stop migrating blind.

The Problem

"We need to move to the cloud." Six words that launch a 12-month project with a 60% failure rate.

Cloud migrations fail because:

  • No assessment: "Let's just move the servers" (lift-and-shift everything, including the problems)
  • Hidden dependencies: App A talks to App B through a hardcoded IP that nobody documented
  • Cost surprises: Cloud costs 3x more than expected because nobody right-sized instances
  • Downtime: Migration window was "1 hour" but took 14 hours because the database was 2TB
  • Security gaps: On-prem firewall rules don't translate to security groups
  • No rollback plan: If the migration fails at 3 AM, now what?

The Solution

The Cloud Migration skill generates complete migration plans with application assessment, the 6 R's strategy assignment (Rehost, Replatform, Refactor, Repurchase, Retire, Retain), dependency mapping, and phased execution timeline.

The Process

View details
You: Plan migration of our infrastructure to AWS:
- 15 application servers (mix of Java, Python, Node.js)
- 3 PostgreSQL databases (largest is 500GB)
- 2 Redis clusters
- 1 RabbitMQ broker
- NFS file storage (2TB)
- On-prem load balancer (F5)
- VPN connections to 3 partner networks
Current spend: $45K/month on colocation

The agent generates a comprehensive migration plan:

Phase 1: Assessment (Week 1-2)

  • Application inventory with dependency matrix
  • Database size and performance profile per DB
  • Network flow analysis (what talks to what)
  • Performance baselines (to compare post-migration)

Phase 2: Strategy Assignment

ApplicationStrategyRationaleTarget Service
Java monolithReplatformToo complex to refactor nowECS Fargate
Python microservices (3)Rehost → RefactorQuick win, then optimizeEC2 → Lambda
Node.js APIs (4)RehostStraightforward containerizationECS Fargate
PostgreSQL primaryReplatformManaged reduces ops burdenRDS Multi-AZ
RedisReplaceManaged is cheaper + HAElastiCache
RabbitMQReplaceManaged equivalent existsAmazon MQ
NFS storageReplatformEFS for shared storageEFS
F5 load balancerReplaceALB is sufficientALB
Legacy reporting appRetireNobody uses it (confirmed)

Phase 3: Execution (6 waves over 12 weeks) Each wave: pre-migration validation → migrate → validate → monitor → sign-off

Phase 4: Optimization (post-migration)

  • Right-sizing instances based on actual usage
  • Reserved instances for predictable workloads
  • Spot instances for batch processing
  • S3 lifecycle policies for cold storage

Projected costs:

ItemOn-PremAWS (Month 1)AWS (Optimized, Month 6)
Compute$18K$22K$14K
Database$12K$8K$6K
Storage$5K$3K$2K
Network$4K$6K$5K
Ops labor$6K$2K$2K
Total$45K$41K$29K

The Results

MetricWing-It MigrationAI-Planned Migration
Planning time2 weeks of meetings2 hours
Hidden dependencies foundDuring migration (panic)During assessment (calm)
Cost surprise+50-200% vs estimate±10% of projection
DowntimeUnplanned, extendedPlanned, minimized
Rollback plan"We'll figure it out"Documented per wave
Success rate~40% on time/budget~85%

Setup on MrChief

yamlShow code
skills:
  - cloud-migration
  - aws
  - terraform      # For IaC on the other side
  - monitoring      # For baseline + post-migration validation
cloud-migrationawsinfrastructure6rs-strategycost-optimization

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Cloud Migration Roadmap — From On-Prem to AWS Without Losing Your Mind — Mr.Chief