What should I complete before starting Azure Migrate assessments?

Complete this 55-question pre-migration checklist before Azure Migrate: (1) Application inventory with business owners identified, (2) Vendor contract status and termination clauses for all applications, (3) Licensing audit showing Software Assurance coverage for Windows/SQL, (4) Disaster recovery commitments and SLA requirements documented, (5) True operating costs including hidden support and maintenance contracts, (6) Network dependency mapping for inter-application communication, (7) Compliance requirements (HIPAA, PCI-DSS, SOC 2) by workload, (8) Data residency restrictions and regulatory constraints. Azure Migrate provides technical assessments but cannot answer organizational readiness questions that finance and legal will block your migration over. Most failed migrations spend 3-6 months on Azure Migrate output without answering the CFO's actual question: What's the 3-year TCO versus current datacenter?

Why do Azure migrations exceed budget and timeline expectations?

Azure migrations exceed budget by 2× and double timelines because organizations start with technical tools (Azure Migrate, CloudEndure) before establishing organizational readiness. Common failures: (1) Discovering application owners don't exist or refuse cloud migration mid-project, (2) Finding vendor contracts require 90-day termination notice after migration planning is complete, (3) Realizing OEM licenses don't transfer to Azure without purchasing new Volume Licenses, (4) Learning applications have undocumented dependencies requiring simultaneous migration, (5) Discovering true operating costs include hidden support contracts not in budgets. Technical assessments are irrelevant if you can't answer 'Who owns this application and will they support it in Azure?' Executive leadership blocks migrations when business questions remain unanswered after months of technical planning.

What questions do CFOs ask about Azure migration that Azure Migrate cannot answer?

CFOs ask five critical questions Azure Migrate cannot answer: (1) What's the 3-year Total Cost of Ownership (TCO) versus current datacenter including hidden costs? Azure Migrate estimates Azure consumption but omits support contracts, vendor fees, training, and organizational change costs. (2) What's the financial risk if migration fails or costs exceed estimates? Need risk-adjusted budget ranges, not single-point estimates. (3) When can we exit datacenter contracts and eliminate those costs? Requires vendor contract analysis and termination clause review. (4) What's the opportunity cost of this migration versus other IT initiatives? Requires business impact assessment beyond technical feasibility. (5) How do we validate ongoing Azure costs won't spiral without proper FinOps governance? Requires cost management framework before migration starts. CFOs block migrations when technical assessments don't address financial risk and organizational readiness.

How do I identify all dependencies for an application before Azure migration?

Identify application dependencies through five complementary methods: (1) Azure Migrate dependency analysis (agent-based or agentless) showing network connections between servers, (2) Application owner interviews documenting known integrations and data flows, (3) Network traffic analysis capturing actual communication patterns over 30+ days, (4) Database connection string analysis in application configs and connection pools, (5) Service account permissions audit showing what systems each app can access. Common hidden dependencies: shared file servers, centralized authentication systems, legacy batch jobs, middleware message queues, and external vendor APIs. Plan minimum 30-day observation period to capture monthly/quarterly processes. Document dependencies in migration wave planning - simultaneous migration of dependent systems reduces failure risk from 40% to 15%.

What licensing issues cause Azure migration audit failures?

Five licensing issues cause Azure migration audit failures: (1) OEM licenses that came with Dell/HP/Lenovo servers don't transfer to Azure - require new Volume Licenses with Software Assurance for Azure Hybrid Benefit, (2) SQL Server licensing audit failures when CAL-based on-premises becomes vCore-based in Azure without proper conversion documentation, (3) Third-party application licenses that prohibit cloud deployment or require expensive cloud licensing upgrades, (4) Windows Server Standard licenses that covered unlimited VMs on physical hosts now require individual licensing per Azure VM, (5) Software Assurance (SA) expiration between migration planning and execution invalidating Azure Hybrid Benefit eligibility. Average audit penalty: $50K-$200K for mid-sized environments. Complete licensing audit 6+ months before migration with legal review of all vendor agreements.

Should I use Azure Migrate for enterprise cloud migration planning?

Use Azure Migrate for technical discovery and sizing AFTER completing organizational readiness. Azure Migrate excels at: (1) VM inventory and right-sizing recommendations, (2) Performance-based sizing using actual CPU/memory utilization, (3) Azure cost estimates based on current usage patterns, (4) Dependency mapping for application grouping. However, Azure Migrate CANNOT answer: (1) Who owns this application and will they support cloud migration? (2) What vendor contracts must be modified or terminated? (3) What compliance requirements affect cloud deployment? (4) What's the true 3-year TCO including hidden costs? (5) What's the organizational change management plan? Start with the 55-question organizational readiness checklist. If you can't answer questions about ownership, licensing, and vendor relationships, Azure Migrate technical output is premature. Technical assessment without organizational readiness causes 60% of migration failures.

Azure Migration: Stop. Don't Migrate Yet.

Short Answer

Most organizations waste 3-6 months on Azure Migrate assessments without completing the 55 critical questions that finance and legal will actually block the project over: application ownership, vendor contract status, licensing compliance, disaster recovery commitments, and true operating costs. This framework prevents $50K-$200K disasters before they happen.

The Conference Room Reality

2019. Leadership announces: "We're going to the cloud."

Finance asks: "What will it cost?"
Leadership: "Less than what we spend now."

IT asks: "Which applications are we migrating?"
Leadership: "All of them."

Someone asks: "How many applications do we have?"

Silence.

Nobody knows.

That's the moment this assessment should have appeared.

Not Azure Migrate. Not CAF documentation. Not consultant proposals.

A systematic framework with 55 questions that expose the gaps before you spend millions.

The 80% Stall (The 'Not My Job' Syndrome)

This is why 70% of migrations fail or stall at the 80% mark. You migrate the easy stuff (Lift & Shift), but when you hit the complex legacy apps, everything stops.
Why? Because the "Cloud Team" thinks the "App Team" owns the refactoring, and the "App Team" thinks the "Cloud Team" owns the server.
Without a clear RACI Matrix, you will hit a wall of "That's not my job" tickets that burn your budget for months.

Why Azure Migrations Fail (Before Any Workloads Move)

Azure Migrate discovers servers. It can't discover:
- ❌ Whether the business owner left the company in 2021
- ❌ Where the installer ISO is stored (or if it exists)
- ❌ If the vendor still exists or supports this version
- ❌ Whether the license allows cloud hosting
- ❌ If anyone actually uses the application

The #1 cause of migration failures isn't technical. It's organizational readiness.

Real Disasters This Framework Prevents

Disaster #1: $30K Licensing Audit

Migrated application to Azure. Vendor audit 6 months later: "Your license is for physical servers only. Cloud license is $50K/year."
Cost: $30K audit penalty + $50K/year ongoing
Prevented by: Question #18 (How is it licensed?)

Disaster #2: $80K Vendor Termination Fees

Migrated without checking vendor contract. Early termination clause discovered after migration.
Cost: $80K in fees
Prevented by: Questions #9 + #21 (Vendor contact + contract expiration)

Disaster #3: Lost Installation Media

Application broke in Azure. Needed rebuild. Installer on Bob's laptop. Bob left in 2019.
Cost: 3 weeks downtime + $50K emergency consulting
Prevented by: Question #17 (Where's the installer stored?)

Disaster #4: Unknown Owner = $52K Annual Waste

Application ran in Azure for 2 years @ $2,200/month. Nobody knew who owned it. Nobody validated it worked.
Cost: $52,800 wasted spend
Prevented by: Question #5 (Who's accountable if this fails?)

Disaster #5: Compliance Failure = 6-Month Delay

Migrated PCI data without proper controls. Failed audit. Had to rebuild with proper isolation.
Cost: 6-month project delay + reputation damage
Prevented by: Question #34 (Which compliance frameworks apply?)

The 55-Question Framework

Download Now

🎯 Get Azure Migration Assessment Pro ($19 - Launch Special)

Professional Excel workbook with:
- ✅ 55 critical pre-migration questions
- ✅ Confidence tracking (High/Med/Low)
- ✅ Owner assignment and collaboration notes
- ✅ Red flag identification system
- ✅ Tested on 100+ enterprise applications

Regular price: $29
Launch price: $19 (ends January 31, 2026)

The 9 Question Categories

1. Identity & Ownership (7 questions)

Who's responsible when it breaks? Who maintains it day-to-day?

2. Vendor & Support (2 questions)

Can we get help when it breaks? Is the vendor still active?

3. Technical Architecture (8 questions)

Platform, OS, dependencies, load balancers, certificates, installers

4. Licensing & Support Contracts (5 questions)

Are we even allowed to run this in Azure? When does support expire?

5. Business Value & Risk (4 questions)

Should we even migrate this? What happens if it's unavailable?

6. Migration Planning (6 questions)

Are we actually ready? Can it be reinstalled from known media?

7. Compliance & Governance (5 questions)

Will this pass audit? PCI? HIPAA? Backup requirements?

8. Cost & Operations (4 questions)

Can we actually afford this? Azure cost vs current cost?

9. Rationalization & Lifecycle (11 questions)

What's the actual plan? Rehost? Refactor? Retire?

How It Works

Week 1: Initial Assessment (30 minutes)

Fill out easy questions (app name, owner, business value)
Mark confidence: High, Medium, or Low
See your readiness status immediately

Week 2: Data Discovery (2-3 hours)

Run KQL queries to auto-fill technical questions
Check vendor contacts and licensing
Update confidence levels

Week 3: Stakeholder Interviews (4-6 hours)

Review Low Confidence answers
Contact business owners, vendors, procurement
Get answers before migration starts

Week 4: Migration Decision

Red Flag Count:
- 0-2 Low Confidence answers = GREEN (ready to migrate)
- 3-5 Low Confidence answers = YELLOW (need discovery work)
- 6+ Low Confidence answers = RED (not ready - high risk)

Red Flags to Watch For

🚩 "I think it's owned by..." → Ownership not validated
🚩 "The person who knew this left in 2020" → Institutional knowledge loss
🚩 "We're not sure where the installer is" → Can't rebuild if it breaks
🚩 "The vendor might still support it" → Licensing risk
🚩 "We'll figure it out after migration" → Recipe for disaster

Each red flag adds risk. Three or more = don't migrate yet.

Azure Migrate vs This Framework

Azure Migrate discovers:
- ✅ VMs, specifications, performance metrics
- ✅ Dependency mapping (technical)
- ✅ Cost estimates based on VM sizing

This framework discovers:
- ✅ Business ownership and accountability
- ✅ Vendor relationships and licensing
- ✅ Compliance requirements
- ✅ Installation and recovery capabilities
- ✅ Strategic value and retirement candidates

You need BOTH.

Azure Migrate = technical inventory
This framework = organizational readiness

Time Saved Per Application

Without this framework:
- 20+ hours per application (discover problems during migration)
- 3-6 weeks project delays from surprises
- $50K-$200K disaster costs

With this framework:
- 2-4 hours per application (discover problems before migration)
- Zero surprises (all red flags identified upfront)
- $0 disaster costs

ROI: 5-10x time savings + disaster prevention

Who This Is For

✅ Azure Architects planning enterprise migrations
✅ Cloud CoEs defining migration standards
✅ IT Directors approving migration budgets
✅ Migration Teams executing migrations
✅ Consultants delivering migration assessments

Battle-Tested In Production

✅ 100+ enterprise applications assessed
✅ Fortune 500 regulated environments (banking, healthcare)
✅ 44 Azure subscriptions
✅ 31,000+ Azure resources
✅ Migrations ranging from $100K to $10M+ budgets

This isn't theory. It's what prevented my own disasters.

Get the Framework

🎯 Azure Migration Assessment Pro - $19

What's included:
- Professional Excel workbook
- 55 questions with confidence tracking
- Data validation dropdowns
- Complete usage instructions
- Lifetime updates
- Commercial license (use with clients)

Launch special: $19 (regular $29)
Ends: January 31, 2026

Get Migration Assessment Pro →

Guarantee

If this framework doesn't save you 5+ hours of discovery work in your first application assessment, email me for a full refund.

No questions asked.

I use this framework myself on every migration. It works.

The Bottom Line

Before Azure Migrate. Before CAF. Before consultants.

Answer these 55 questions for every application.

If you can't answer 50% with high confidence, you're not ready to migrate yet.

That's not failure. That's clarity.

Discovering you're not ready on Day 1 costs $0.

Discovering you're not ready in Month 18 after spending millions? That's expensive.

This framework is what I wish I'd had in 2019.

You have it now. Use it.

Additional Resources

From the Migration Hub:
- Complete Azure Migration Guide
- Application Migration Checklist
- Migration Yard Sale: What Not to Migrate

Want more operational reality checks? Browse the Content Hubs for Azure content that addresses the problems Microsoft's documentation ignores.

🛑 The "Pre-Flight Checklist" You Are Missing

You wouldn't let a pilot fly without a checklist. Don't let your team migrate without a defined RACI.
Ensure every server, database, and application has a signed-off owner before the migration truck leaves the dock.

Download the Azure RACI Matrix Template

It includes the specific "Migration-Ready" roles you need to assign to prevent the 80% stall.

Get the RACI Migration Checklist