Windows Server Migration Checklist for Small Businesses

A Windows Server migration checklist helps small businesses move users, apps, files, databases, Remote Desktop access, and backups without turning the cutover into guesswork. Before migrating to a new Windows Server or cloud Windows VPS, document what the old server does, test the destination, protect the data, plan rollback, and move production only after users can complete real workflows. Raff Technologies provides Windows VMs and Windows migration support for teams that want to move Windows workloads to cloud-hosted infrastructure.

A server migration is not only an operating system task. It is a business continuity task. The server may hold files, accounting software, SQL Server databases, Active Directory, Remote Desktop users, IIS apps, printers, scheduled jobs, certificates, mapped drives, and vendor software.

That is why small businesses should not start with “copy everything to the new server.” Start with the checklist. Then decide what should migrate, what should be rebuilt, what should be retired, and what needs a test before the cutover.

Quick migration checklist

Use this table as the short version before starting the project.

The goal is not to make migration complicated. The goal is to prevent surprises after users start working on the new server.

Why migration planning matters for small businesses

Small businesses often run a lot of business logic on one server. The server may have started as a file share, then gained accounting software, remote users, SQL Server, printers, scheduled exports, vendor tools, and backup jobs over time.

That creates hidden migration risk.

Common hidden dependencies include:

A migration checklist forces those issues into the open before the cutover.

Choose the migration approach first

Microsoft describes several methods for moving to a newer Windows Server version, including in-place upgrade, clean install, migration, cluster rolling upgrade, and edition conversion. Each method has different trade-offs for downtime, complexity, and hardware requirements.

For small businesses, the most common choices are:

For Raff Windows VPS migrations, side-by-side migration is usually the cleaner model. You build the destination Windows VM, test it, copy data, verify apps, then cut over users.

Phase 1: inventory the current server

Do not migrate what you do not understand. Start with inventory.

Document:

Write this down before touching the destination server. Many migration problems are actually discovery problems.

Phase 2: decide what moves and what retires

Migration is a good moment to clean up. Not everything should move.

Sort workloads into four groups:

Examples:

Moving every old folder and app without review creates a new server with old clutter.

Phase 3: choose the destination environment

For small businesses, the destination is usually one of three options:

A Windows VPS is a strong fit when the business needs:

• Remote Desktop access
• shared Windows apps
• cloud file server workloads
• accounting or tax software
• Microsoft Access or legacy apps
• ERP or inventory software
• SQL Server tools
• IIS/.NET workloads
• a replacement for aging office hardware

It is not always the right fit for high-availability architectures, heavy LAN-only file workloads, unsupported vendor apps, or local hardware dependencies that have not been tested.

Phase 4: plan remote access and user sessions

If users will access the new server remotely, plan the access model before migration.

Use this table:

Microsoft states that each user or device connecting to an RD Session Host running Windows Server needs an RDS Client Access License. Build that into migration planning before staff start using the new server daily.

Remote access is not just a port. It affects licensing, security, user experience, support, and backup risk.

Phase 5: protect the source before changing anything

Before migration work begins, protect the current environment.

Do this before the first major change:

A backup that has never been restored is an assumption. At minimum, test restoring a file, a folder, and one business-critical app or database backup before cutover.

Phase 6: build the destination server cleanly

Build the destination before moving production data.

For a Windows VPS destination, prepare:

Do not build the new server in a hurry and then try to harden it later. Production hardening should happen before cutover.

Phase 7: migrate file shares carefully

File server migration is often more sensitive than it looks. Users care about folder paths, permissions, mapped drives, and file versions.

For file shares, document:

Microsoft’s Storage Migration Service is designed to inventory servers, transfer data to newer Windows servers or Azure virtual machines, and optionally transfer the source server identity so apps and users do not need to change links or paths. For SMB file server migrations, that tool can be useful when the migration scope fits.

Phase 8: migrate applications and dependencies

Business apps are usually the hardest part of the migration.

Before installing or moving an app, confirm:

Do not judge migration success by whether the app opens. Test real workflows: create a record, edit data, run a report, export a file, print, email, sync, and close the day.

Phase 9: handle SQL Server and databases separately

SQL Server migration needs its own plan. Copying database files is not the same as a validated database migration.

For SQL Server, check:

Microsoft documents SQL Server database copy by backup and restore, and SQL Server backup/restore planning includes strategy and security considerations. For small businesses, backup/restore is often the cleanest migration method because it creates a repeatable test before production cutover.

If the app depends on SQL Server, test the app against the restored database on the new server before scheduling cutover.

Phase 10: plan Active Directory carefully

Active Directory migration is not a casual copy operation. If the old server is a domain controller, DNS server, or FSMO role holder, migration must be planned carefully.

Check:

Microsoft provides documentation for transferring FSMO roles in Active Directory Domain Services. If AD is involved, keep this article as a checklist and use a dedicated AD migration plan for the technical work.

For many small businesses, AD migration is the point where it is worth talking to an engineer instead of improvising.

Phase 11: test with real users

A migration is not validated until real users can complete real work.

Test:

Do not let only the technical admin test the new server. Include the person who uses the accounting app, the person who prints labels, the person who runs reports, and the person who needs remote access.

Phase 12: plan the cutover window

A cutover should have a written sequence.

Example cutover plan:

1. Announce downtime window.
2. Confirm latest source backup.
3. Freeze writes on the old server.
4. Stop relevant services or app access.
5. Run final file/database sync.
6. Restore or attach final database on destination.
7. Update DNS, mapped drives, shortcuts, or connection strings.
8. Start destination services.
9. Test admin login.
10. Test user login.
11. Test files, apps, reports, printing, and backups.
12. Confirm users can work.
13. Keep old server online but read-only or isolated.
14. Monitor logs and user reports after launch.

The cutover should be boring. If it feels exciting, too much was left unknown.

Phase 13: keep rollback available

Rollback is not failure. It is risk management.

Before cutover, define:

Keep the old environment available until the new one is proven. Do not wipe or repurpose the old server immediately after first login works.

Phase 14: monitor after migration

The first week after migration matters.

Monitor:

Migration is not done when the old server is shut down. It is done when the new server is stable, backed up, documented, and users can work normally.

Checklist by workload type

Different server roles need different migration attention.

This is why one generic migration plan is not enough. Use the checklist as the control layer, then use workload-specific guides for detailed execution.

How Raff fits Windows Server migration

Raff fits Windows Server migration when a small business wants to move from an aging office server, unsupported Windows Server version, branch server, or local business software environment to a cloud-hosted Windows Server VM.

Raff Windows VMs can serve as the destination for Remote Desktop environments, business apps, cloud file servers, SQL Server tools, Access and legacy apps, tax software, ERP/inventory workloads, and MSP-managed client environments.

Raff is not a replacement for application vendor support, licensing review, or workload-specific testing. The clean model is: use Raff for the Windows VM infrastructure, then migrate with a clear plan for apps, users, files, databases, backups, access, and cutover.

Final pre-cutover checklist

Before production cutover, confirm:

If any line is unclear, pause before moving production users.

What's next

• Review Raff’s Windows Server migration service if you want migration help.
• Read How to Migrate Windows Server 2016 to 2025 if your source server is still Windows Server 2016.
• Read Cloud Windows Server vs Local Office Server if you are deciding whether to keep local hardware.
• Read Windows VPS sizing for remote users before choosing CPU, RAM, and storage.
• Read Windows VPS Backup Strategy for Small Businesses before migrating production data.
• Read Remote Desktop Gateway vs Direct RDP before exposing remote access.
• Read Windows VPS as a Cloud File Server if file shares are part of the migration.
• Review Raff Windows VM and pricing when planning the destination server.

Sources

• Microsoft Learn — Plan Your Windows Server Upgrade Path
• Microsoft Learn — Upgrade and migrate roles and features in Windows Server
• Microsoft Support — Support for Windows Server 2016 will end in January 2027
• Microsoft Learn — Storage Migration Service overview
• Microsoft Learn — Migrate a file server by using Storage Migration Service
• Microsoft Learn — License Remote Desktop Services with Client Access Licenses
• Microsoft Learn — Back up and restore of SQL Server databases
• Microsoft Learn — Copy databases with backup and restore
• Microsoft Learn — Transfer FSMO roles in Active Directory Domain Services
• Microsoft Learn — Backup and Storage overview for Windows Server
• Raff — Windows Server migration service
• Raff — Windows VM product page
• Raff — Pricing