Migrating to Azure can transform your infrastructure, but poor planning leads to cost overruns, downtime, and security gaps. This checklist covers the key steps for a successful migration.
Phase 1: Discovery and Assessment
Inventory Your Current Infrastructure
Document everything you're running:
- Applications and dependencies
- Databases and data stores
- Network architecture and firewall rules
- Authentication and authorization systems
- Backup and disaster recovery procedures
Assess Migration Readiness
Not everything should move to the cloud immediately:
Good Candidates for Migration:
- Web applications with variable traffic
- Development and test environments
- Databases with growth needs
- Applications requiring global availability
Consider Carefully:
- Legacy applications with hardware dependencies
- Systems with strict compliance requirements
- Applications with very stable, predictable workloads
- Systems approaching end-of-life
Calculate Total Cost of Ownership (TCO)
Use Azure's TCO calculator, but don't forget:
- Migration costs (tools, consulting, labor)
- Training and skill development
- Ongoing management and monitoring
- Data egress charges
- License portability (Azure Hybrid Benefit)
Phase 2: Planning
Choose Your Migration Strategy
Different workloads need different approaches:
Rehost (Lift and Shift)
- Quickest migration path
- Minimal code changes
- Use Azure Migrate for VMs
- Good for: Legacy apps, quick wins
Replatform (Lift and Optimize)
- Migrate to PaaS where possible
- Moderate optimization
- Example: SQL Server VM → Azure SQL Database
- Good for: Standard web apps, databases
Refactor (Rearchitect)
- Redesign for cloud-native
- Maximum benefits, highest effort
- Example: Monolith → Microservices
- Good for: Core business applications
Design Your Azure Architecture
Key decisions to make:
Subscription Structure
- One subscription per environment?
- Per department or per application?
- Use management groups for governance
Networking
- Hub-and-spoke topology for enterprise
- Express Route vs. VPN for hybrid connectivity
- Network security groups and firewalls
- Private endpoints for PaaS services
Identity and Access
- Azure AD integration
- Role-based access control (RBAC)
- Privileged Identity Management (PIM)
- Conditional access policies
Resource Organization
- Naming conventions
- Tagging strategy (cost center, environment, owner)
- Resource groups per workload or lifecycle
Phase 3: Security and Compliance
Implement Security Baselines
Before migrating workloads:
Network Security
- Enable Azure DDoS Protection
- Configure Network Security Groups (NSGs)
- Implement Azure Firewall or NVAs
- Use Private Link for PaaS services
Identity Security
- Enforce multi-factor authentication (MFA)
- Implement Conditional Access
- Enable Azure AD Identity Protection
- Use managed identities instead of keys/passwords
Data Protection
- Enable encryption at rest (default for most services)
- Use Azure Key Vault for secrets management
- Implement Azure Backup
- Configure Azure Site Recovery for DR
Monitoring and Compliance
- Enable Azure Security Center
- Configure Azure Sentinel for SIEM
- Use Azure Policy for governance
- Enable diagnostic logging
Compliance Requirements
Ensure your design meets regulatory needs:
- HIPAA, PCI-DSS, SOC 2, etc.
- Data residency requirements
- Audit and reporting capabilities
- Backup retention policies
Phase 4: Migration Execution
Pilot Migration
Start small to validate your approach:
- Choose a low-risk, non-critical workload
- Document the entire migration process
- Test thoroughly in Azure
- Measure performance and costs
- Gather lessons learned
Migration Tools
Azure Migrate
- Discovery and assessment
- Agentless VM migration
- Database migration assessment
Azure Site Recovery
- VM replication and failover
- Physical server migration
- Disaster recovery testing
Azure Database Migration Service
- Minimal downtime database migrations
- Support for SQL, MySQL, PostgreSQL
- Schema and data migration
Data Migration Strategy
Moving large amounts of data:
Small Datasets (< 1 TB)
- Azure Data Box
- Direct upload over internet
Large Datasets (> 1 TB)
- Azure Data Box (physical device)
- Azure Import/Export service
- Consider bandwidth and time constraints
Phase 5: Optimization
Cost Management
After migration, optimize spending:
- Right-size VMs based on actual usage
- Use Reserved Instances for stable workloads
- Implement auto-scaling
- Set up budget alerts
- Use Azure Advisor recommendations
Performance Tuning
- Enable Application Insights for monitoring
- Use Azure Monitor for infrastructure metrics
- Configure auto-scaling rules
- Optimize database performance (indexing, caching)
Governance
Maintain control as you scale:
- Implement Azure Policy for compliance
- Use Azure Blueprints for repeatable deployments
- Set up cost allocation with tags
- Regular access reviews
Common Pitfalls
1. Underestimating Complexity
- Dependencies are often more complex than documented
- Test thoroughly before cutover
2. Ignoring Networking
- Bandwidth constraints cause delays
- Latency impacts application performance
3. Forgetting About Monitoring
- Set up monitoring before migration
- Establish baseline metrics
4. Skipping Security
- Security should be built-in, not bolted-on
- Follow least-privilege principles
5. No Rollback Plan
- Always have a way to roll back
- Test your rollback procedure
Post-Migration Checklist
After going live:
- Verify all applications are functional
- Validate backup and recovery procedures
- Confirm monitoring and alerting
- Review security configurations
- Update documentation
- Train operations team
- Decommission old infrastructure (after grace period)
Takeaway
Successful Azure migrations require careful planning, phased execution, and continuous optimization. Start with a pilot, use the right tools, and don't rush the security and compliance steps.
The cloud's flexibility is powerful—but only if you build on solid foundations.
Need help with your Azure migration? Our Azure Cloud Services team has migrated hundreds of workloads. Schedule a consultation to discuss your needs.