AWS Migration Checklist for Small Businesses

A successful AWS migration is mostly preparation. The technical move of a server with AWS Application Migration Service can take hours; discovering what that server depends on, building a secure place to put it and agreeing on a cutover window takes much longer. This checklist reflects the sequence we use for small businesses and nonprofits and supports the process on our AWS consulting page.

What should you do before migrating to AWS?

Inventory everything, understand dependencies and define what success looks like. Skipping discovery is the most common cause of failed or delayed migrations.

Discovery checklist

• ☐List every server, application, database, file share and scheduled job, with a business owner and criticality rating.
• ☐Collect utilization data (CPU, memory, disk, network) for at least two weeks using AWS Application Discovery Service, Migration Evaluator or your existing monitoring.
• ☐Map dependencies, such as which apps talk to which databases, file shares, license servers and external services.
• ☐Record OS and database versions and flag anything out of support.
• ☐Identify Microsoft licensing constraints, since bring-your-own-license rules on AWS differ from Azure.
• ☐Document compliance requirements (HIPAA, PCI DSS, data residency) and choose a region, often us-west-2 (Oregon) for Pacific Northwest organizations.
• ☐Define acceptable downtime per application, success criteria and budget.

If you are still deciding whether to move, start with a cloud readiness assessment, or compare platforms in Azure vs AWS.

How do you prepare your AWS environment?

Build a multi-account landing zone with identity, logging, networking and guardrails before any production workload arrives. It is far harder to untangle a single shared account later.

Landing zone checklist

• ☐Set up AWS Organizations and AWS Control Tower with separate accounts for production, non-production, shared services, log archive and audit.
• ☐Configure IAM Identity Center for single sign-on with MFA, and lock away the root user of every account.
• ☐Enable organization-wide AWS CloudTrail, AWS Config, Amazon GuardDuty and AWS Security Hub.
• ☐Design VPCs with private subnets for servers and databases, and connect offices with AWS Site-to-Site VPN or AWS Direct Connect.
• ☐Plan DNS with Amazon Route 53 and any hybrid name resolution needed for Active Directory.
• ☐Set AWS Budgets alerts and a tagging policy for owner, environment and cost center.
• ☐Define the foundation with Terraform or AWS CloudFormation.

Our AWS landing zone guide covers account structure and guardrails in detail.

Which migration strategy fits each workload?

Pick a strategy per workload based on business value, effort and risk. AWS describes these as the 7 Rs, and most small business migrations use three or four of them.

Read more in our guide to the 7 Rs of cloud migration.

How do you run the pilot and migration waves?

Pilot one low-risk workload end to end, then migrate the rest in dependency-based waves. Every cutover should be tested in advance and reversible.

Pilot checklist

• ☐Install the AWS Replication Agent on the source server and let initial replication complete.
• ☐Configure launch templates with the right instance type, subnet and security groups.
• ☐Launch a test instance, validate the application, logins, integrations and performance.
• ☐Time each step and write a runbook with a rollback plan.

Wave checklist

• ☐Group servers that depend on each other into the same wave.
• ☐Announce the cutover window and freeze changes.
• ☐Stop the application on the source, allow final replication, and launch cutover instances.
• ☐Update DNS, connection strings and firewall rules.
• ☐Have application owners test and sign off.
• ☐Keep the source intact for an agreed rollback period, then finalize the cutover in the console.

Database and file data

Use AWS Database Migration Service for minimal-downtime database moves or engine changes, and AWS DataSync for file shares into Amazon S3, Amazon EFS or Amazon FSx. See our data migration guide for planning large transfers.

What should you do after migrating to AWS?

Harden, optimize and decommission in the first 30-60 days. This is when most waste and misconfiguration can be fixed cheaply.

Post-migration checklist

• ☐Configure AWS Backup plans and perform a test restore.
• ☐Review Security Hub findings and remediate critical and high items.
• ☐Set Amazon CloudWatch alarms for availability, CPU, disk and status checks.
• ☐Remove replication servers and staging resources left over from migration.
• ☐Right-size instances using AWS Compute Optimizer after a few weeks of data.
• ☐Purchase Savings Plans only for stable baseline usage.
• ☐Securely wipe and retire on-premises hardware.
• ☐Update documentation and train the team that will run the environment.

Our AWS cost optimization guide and AWS Well-Architected review cover the next steps.

Common AWS migration mistakes

Most problems are avoidable with planning.

• One account for everything, which mixes production with experiments and makes access control hard.
• Copying on-premises sizes rather than using measured utilization.
• Forgetting Windows licensing, which can change the cost of Windows and SQL Server workloads.
• Open security groups created during testing and never tightened.
• Leaving migration infrastructure running after cutover.

How Desai InfoTech helps with AWS migrations

Desai InfoTech plans and runs AWS migrations for small businesses and nonprofits, starting with discovery and a pilot so you can see the approach work before committing. Request a free cloud assessment to get started.