1. Inventory the current server
- Edition, build, patch state and activation method
- Physical or virtual platform, CPU, memory, disks and storage layout
- Server roles and features
- Installed applications, services and runtimes
- Shares, printers, scheduled tasks and scripts
- Certificates, service accounts and local accounts
2. Map identity and network dependencies
- Active Directory roles, FSMO ownership and Global Catalog status
- DNS zones, forwarders and application records
- DHCP scopes, reservations and options
- Static IPs, VLANs, routes, NAT and firewall policies
- VPN, remote-access and public-IP dependencies
3. Prove recovery before change
Confirm what is backed up, where it is stored, how recent it is, whether the backup copy is isolated from production credentials, and whether a restore has been tested. For a migration, define both the recovery point and the rollback trigger before the cutover begins.
4. Confirm application compatibility
Do not assume a line-of-business application supports Windows Server 2022 or 2025 because it runs on 2016. Check the vendor's supported OS, database version, .NET/runtime requirements, licensing mechanism and any hard-coded server names or IP addresses.
5. Choose the destination and migration method
Decide whether the best path is an in-place upgrade, a new server or VM, role migration, application rebuild, physical-to-virtual move, consolidation or retirement. Microsoft's Windows Server upgrade documentation lists supported upgrade methods and restrictions; application support may be more restrictive than the operating system itself.
6. Define the cutover
- Maintenance window and business owner approval
- Final backup or synchronization point
- Sequence of services and applications to stop
- DNS/IP/name changes
- Data synchronization method
- Rollback decision point and source preservation
7. Validate the new environment
- Authentication and user access
- Applications and dependent services
- DNS, routes, firewall rules and remote access
- File permissions and shares
- Scheduled jobs and integrations
- Monitoring, EDR and backup jobs
- Post-migration restore capability