☁️ Enterprise Migration Reality

This guide is part of our Azure Governance hub covering policy enforcement, compliance frameworks, and enterprise controls.

The unfiltered guide to Azure migrations that actually work.

Most Azure migration content focuses on the technical how-to. This hub addresses the organizational, financial, and operational reality that determines whether migrations succeed or fail.

If you're planning, executing, or recovering from an Azure migration—this is your reference library.

📋 Start Here: Pre-Migration Planning

Before you migrate anything, answer these questions:

💰 Migration ROI & Financial Reality

Finance will ask: "What's the ROI?" Here's how to answer.

Why Your Azure Migration ROI Calculation Is Wrong

Finance compares server costs. That's not what changes.

What actually changes:
- 6-month procurement cycles → Same-day provisioning
- VAR meetings eliminated
- Hardware refresh projects eliminated
- CapEx approval barriers removed
- Marketplace software procurement in minutes

The real ROI: Business agility, not server savings.

Read the ROI reality check →

Azure Hybrid Benefit: The $50K Licensing Mistake

Most enterprises accidentally trigger $50K+ audit penalties by misusing Azure Hybrid Benefit.

Common mistakes:
- Applying AHB without active Software Assurance
- No proof of purchase documentation
- Wrong core-to-VM mapping
- Double-paying on marketplace images

5-question checklist before enabling AHB.

Read the licensing guide →

🎯 Application Migration Planning

Application Migration Checklist for Azure

The 55-question assessment for EACH application.

Categories covered:
- Identity & Ownership (7 questions)
- Vendor & Support (6 questions)
- Technical Architecture (8 questions)
- Licensing & Contracts (5 questions)
- Business Value & Risk (4 questions)
- Migration Planning (6 questions)
- Compliance & Governance (5 questions)
- Cost & Operations (9 questions)
- Rationalization & Lifecycle (5 questions)

Download the Excel template and fill it out BEFORE migrating.

Get the complete checklist →

⚠️ Common Migration Failures

Why Most Azure Migrations Fail

The organizational problems that kill migrations before they start.

Real failure patterns:
- Migrating applications nobody uses ($32K wasted)
- Lost installation media (can't rebuild)
- No business owner (nobody to approve)
- Vendor licensing restrictions ($75K surprise)
- Certificate expirations (12 days downtime)
- Compliance violations ($95K remediation)

Each mistake has the same root cause: Incomplete discovery.

Learn from migration failures →

Azure Migration Yard Sale Rolloff

What happens when you skip rationalization and just "migrate everything."

The pattern:
- Lift-and-shift 500 VMs to Azure
- Discover 40% were unused
- Spend months identifying retirement candidates
- Post-migration cleanup costs more than migration

Rationalize BEFORE migrating, not after.

Read the yard sale story →

🔧 Migration Execution

Azure Migrate: Enterprise Hybrid Reality

How Azure Migrate actually works in complex enterprise environments.

Covers:
- Discovery across multiple VMware environments
- Dependency mapping at scale
- Assessment accuracy and limitations
- Migration wave planning
- Post-migration validation

Azure Migrate is excellent—when you use it correctly.

Read the execution guide →

📊 Cost Management Post-Migration

You migrated. Now what does it cost?

Azure FinOps 2025: Complete Guide

How to actually understand and control Azure costs.

Covers:
- Tag governance (the 247 variations problem)
- Application-level cost visibility
- Chargeback models that business units accept
- Shared services allocation
- What optimization actually works

FinOps isn't about cutting costs. It's about understanding them.

Read the FinOps guide →

Azure Tagging Best Practices 2025

Tag governance is the foundation of cost allocation.

The mistakes that break reporting:
- 247 variations of "Production"
- Missing cost center tags
- No enforcement via Azure Policy
- Retrofit tagging after migration

Get tagging right BEFORE migration, not after.

Read the tagging guide →

🎓 Migration Lessons Learned

The Institutional Knowledge Problem

When the person who knew how things work left 3 years ago.

What you lose:
- Application architecture knowledge
- Vendor relationships
- License agreement details
- Certificate locations
- Integration dependencies

Document everything like everyone is leaving tomorrow.

PowerShell 7 Enterprise Migration

Migrating enterprise PowerShell scripts to Azure automation.

Covers:
- PowerShell 5.1 vs 7.x differences
- Module compatibility issues
- Azure Automation limitations
- Runbook migration patterns

Not every script migrates cleanly.

Read the PowerShell migration guide →

📥 Migration Resources

Downloads

• 55-Question Application Questionnaire (Excel)
• Application Questionnaire (CSV)
• Azure RACI Template (PDF)
• KQL Query Library (PDF)

Related Hubs

• ☁️ FinOps Hub - Cost management and optimization
• 🔒 Governance Hub - Policy, compliance, and controls
• 🛠️ Operations Hub - Day-to-day Azure management

💡 Key Principles

From 31,000+ resources across 44 subscriptions in regulated banking:

1. Discovery before migration - Can't migrate what you don't understand
2. Rationalize before rehosting - 20-40% should be retired, not migrated
3. Document institutional knowledge - People leave, documentation stays
4. Validate licenses BEFORE migrating - $50K audit penalties are real
5. Tag during migration - Retroactive tagging costs 10x more
6. ROI isn't server costs - It's procurement cycles eliminated
7. Plan for the 6-month audit - Microsoft will verify your AHB usage
8. Applications without owners - Are retirement candidates, not migration candidates

🚀 Migration Roadmap

Phase 1: Discovery (Months 1-3)
- Deploy Azure Migrate for technical discovery
- Complete 55-question questionnaire per application
- Identify retirement candidates
- Map dependencies

Phase 2: Rationalization (Months 3-4)
- Decide 7R action per application (Rehost, Refactor, Rearchitect, Rebuild, Replace, Retire, Retain)
- Calculate actual costs (including all hidden costs)
- Validate licensing compliance
- Get business owner approval

Phase 3: Planning (Months 4-6)
- Design landing zones
- Implement tag governance
- Configure compliance policies
- Prepare migration waves

Phase 4: Pilot (Months 6-9)
- Migrate 5-10 low-risk applications
- Validate approach
- Document lessons learned
- Adjust process

Phase 5: Execution (Months 9-24)
- Wave-based migrations
- Post-migration validation
- Cost optimization
- Continuous improvement

Realistic timeline: 18-24 months for 100+ applications

❓ Common Questions

Q: Can we accelerate the timeline?
A: Yes, if you skip discovery and pay 2x later when things break.

Q: Do we need consultants?
A: For complex migrations, yes. For organizational readiness, no—use the questionnaire.

Q: What's the biggest risk?
A: Migrating applications you should have retired instead.

Q: How much will Azure cost vs. on-premises?
A: Compute might be 30% more, but procurement cycles are eliminated. ROI is operational, not per-VM.

Q: Should we use Azure Hybrid Benefit?
A: Only if you have active SA, proof of purchase, and correct core mapping. Read the licensing guide first.

📧 Stay Updated

Migration guidance, operational lessons, and cost management strategies—delivered when I learn something worth sharing.

No fluff. No vendor pitches. Just operational reality.

Built from real experience managing 31,000+ Azure resources in regulated banking.

No theory. No best practices that don't work. Just what actually happens.

Last updated: December 2025