Cloud Migration Checklist: Moving Your Business to the Cloud

Why Cloud Migration Is No Longer Optional

The question for Canadian businesses is no longer whether to move to the cloud, but how to do it right. Cloud computing offers compelling advantages — reduced capital expenditure, improved scalability, enhanced collaboration, and access to enterprise-grade infrastructure without enterprise-grade budgets.

But cloud migration is not as simple as uploading files to a server. Without proper planning, businesses encounter data loss, extended downtime, unexpected costs, and security vulnerabilities. This comprehensive checklist will guide you through every phase of a successful cloud migration.

Phase 1: Assessment and Discovery

Before moving anything to the cloud, you need a clear picture of what you have and where you want to go.

Inventory Your Current Infrastructure

Document every system, application, and data store in your current environment:

• Servers — Physical and virtual servers, their specifications, operating systems, and roles
• Applications — Every business application, including version numbers, dependencies, and licensing terms
• Data stores — Databases, file shares, email archives, and their sizes
• Network architecture — IP schemes, firewall rules, VPN configurations, and DNS records
• User access — Who accesses what, from where, and how (VPN, direct, remote desktop)
• Integration points — How systems communicate with each other and with external services

Classify Your Workloads

Not every workload belongs in the cloud, and not every workload should migrate at the same time. Classify each workload into one of these categories:

1. Rehost (Lift and Shift) — Move the workload to the cloud as-is with minimal changes. Fastest migration path but doesn't optimize for cloud-native benefits
2. Replatform — Make minor optimizations during migration, such as moving a database to a managed cloud database service while keeping the application mostly unchanged
3. Refactor — Redesign the application to take full advantage of cloud-native services. Most time-intensive but delivers the greatest long-term benefits
4. Replace — Retire the legacy application and replace it with a cloud-native SaaS alternative
5. Retain — Keep the workload on-premises due to compliance requirements, latency sensitivity, or other technical constraints
6. Retire — Decommission applications that are no longer needed

Pro Tip: Start with workloads that are easy to migrate and low-risk. Early successes build confidence and reveal lessons that benefit more complex migrations later.

Phase 2: Planning and Design

With your assessment complete, it's time to design your cloud environment and create a detailed migration plan.

Choose Your Cloud Platform

The three major public cloud platforms each have strengths:

• Microsoft Azure — Best integration with Microsoft ecosystems (Active Directory, Office 365, SQL Server). Strong choice for businesses already invested in Microsoft technologies
• Amazon Web Services (AWS) — Broadest service catalogue and largest global infrastructure. Excellent for businesses needing maximum flexibility and scale
• Google Cloud Platform (GCP) — Strong in data analytics, machine learning, and Kubernetes. Attractive pricing models for data-intensive workloads

For many Canadian small and mid-sized businesses, Microsoft Azure is the natural choice due to its seamless integration with Microsoft 365 and Active Directory — tools most businesses already use daily.

Design Your Cloud Architecture

• Networking — Design your virtual network topology, including subnets, security groups, and connectivity back to your office (VPN or dedicated connection)
• Identity and access — Plan how users will authenticate and what permissions they'll have. Azure Active Directory or AWS IAM should be configured with least-privilege access principles
• Security — Define your security architecture including encryption at rest and in transit, firewall rules, intrusion detection, and compliance controls
• Backup and disaster recovery — Design your backup strategy and recovery procedures before migration, not after
• Cost management — Establish budgets, set up cost alerts, and choose the right instance sizes. Cloud costs can escalate quickly without proper governance

Create a Migration Timeline

Map out the sequence of migrations with realistic timelines:

1. Migrate non-critical workloads first as a pilot
2. Schedule critical system migrations during low-usage periods (evenings, weekends)
3. Build in buffer time — migrations almost always take longer than estimated
4. Plan for parallel running periods where both old and new systems operate simultaneously
5. Define clear rollback procedures for each migration phase

Phase 3: Preparation

The preparation phase sets the stage for a smooth migration execution.

Pre-Migration Checklist

• Upgrade dependencies — Ensure operating systems, databases, and applications meet the cloud platform's minimum requirements
• Clean up data — Don't migrate data you don't need. Archive old files, purge temporary data, and consolidate duplicate records
• Test connectivity — Verify VPN or dedicated connections between your office and the cloud environment are stable and performant
• Train your team — Ensure IT staff understand the cloud platform's management tools and your team knows what to expect during the transition
• Communicate with stakeholders — Inform all affected employees about the migration timeline, expected changes, and any anticipated downtime
• Verify backups — Confirm that complete, tested backups of all systems exist before any migration begins. This is your safety net

Phase 4: Migration Execution

With planning and preparation complete, it's time to execute. Follow your migration plan methodically.

Migration Day Procedures

1. Final backup — Take one last backup of the system being migrated immediately before starting
2. Execute migration — Use the appropriate migration tool for your platform (Azure Migrate, AWS Migration Hub, or GCP Migrate)
3. Verify data integrity — Compare file counts, database record counts, and checksums between source and destination
4. Test functionality — Systematically test every application function, integration point, and user workflow
5. Update DNS and networking — Redirect traffic from old systems to new cloud systems
6. Monitor closely — Watch performance metrics, error logs, and user reports intensively for the first 48-72 hours

Rollback Triggers

Define specific conditions that trigger a rollback to the original system:

• Data integrity failures detected during verification
• Critical application functionality broken after migration
• Performance degradation exceeding acceptable thresholds
• Security incidents detected during or immediately after migration

Phase 5: Optimization and Governance

Migration is not the finish line — it's the starting point. Post-migration optimization ensures you get maximum value from your cloud investment.

Ongoing Optimization Tasks

• Right-size resources — Monitor actual usage and adjust instance sizes. Many businesses over-provision initially, paying for capacity they don't use
• Implement auto-scaling — Configure resources to scale up during peak demand and scale down during quiet periods
• Review reserved instances — For steady-state workloads, reserved instances (1-3 year commitments) save 30-60% compared to on-demand pricing
• Enable cost tagging — Tag all resources by department, project, or environment so you can track spending accurately
• Schedule non-production resources — Development and testing environments don't need to run 24/7. Automate shutdown during non-business hours

Let TechBoss Guide Your Cloud Migration

Cloud migration is a significant undertaking that benefits enormously from experienced guidance. At TechBoss, we've helped dozens of Canadian businesses migrate to the cloud — from simple email migrations to complex multi-server infrastructure projects.

Our team handles the technical complexity so you can focus on running your business. We assess your current environment, design your cloud architecture, execute the migration, and provide ongoing optimization and support.

Ready to start your cloud journey? Request a free consultation or contact our cloud team to discuss your migration project.