Complete Migration Guide
Upgrading a Windows Server is not the same as updating a workstation.
A failed desktop upgrade may affect one user.
A failed server upgrade can interrupt authentication, file access, business applications, backups, or services used by an entire organization.
That is why the first step in a Windows Server 2025 upgrade is not mounting an ISO file.
The first step is understanding the server you are about to change.
What roles does it run?
Which applications depend on it?
Can the application vendor support Windows Server 2025?
Is the server physical or virtual?
Do you have a tested recovery path if the upgrade does not complete?
Windows Server 2022 can be upgraded directly to Windows Server 2025 in supported configurations. An in-place upgrade can preserve installed roles, applications, settings, and data, making it an attractive option for many existing servers.
That does not mean every production server should automatically be upgraded in place.
In some environments, deploying a new Windows Server 2025 system and migrating the workload is the cleaner approach.
This guide explains how to plan an upgrade from Windows Server 2022 to Windows Server 2025, when to consider an in-place upgrade, when migration may be safer, and what to verify before and after the operating system changes.
If you are planning a new server instead of upgrading an existing deployment, follow our Windows Server 2025 Installation Guide.
For hardware compatibility, review the Windows Server 2025 System Requirements Guide.
Table of Contents
- Can You Upgrade Windows Server 2022 to 2025?
- In-Place Upgrade vs Clean Migration
- When an In-Place Upgrade Makes Sense
- When a Clean Migration May Be Better
- Check Windows Server Edition and Installation Type
- Check Application Compatibility
- Review Server Roles
- Create a Backup and Recovery Plan
- Prepare Windows Server 2022 for the Upgrade
- How to Upgrade Windows Server 2022 to 2025
- Verify the Server After the Upgrade
- Upgrading Domain Controllers
- Upgrading Hyper-V Hosts
- Common Windows Server Upgrade Problems
- Windows Server 2025 Upgrade Checklist
- Frequently Asked Questions
Can You Upgrade Windows Server 2022 to Windows Server 2025?
Yes. Windows Server 2022 has a supported direct upgrade path to Windows Server 2025 in applicable configurations.
This is an in-place operating system upgrade.
The existing Windows Server installation is upgraded to the newer operating system while compatible settings, server roles, applications, and data can remain on the server.
For example, a server may start as:
Windows Server 2022 Standard
and be upgraded through a supported path to:
Windows Server 2025 Standard
The physical or virtual server remains the same system.
You are changing the operating system version rather than deploying a completely separate server and manually moving the workload.
Windows Server 2025 also expands direct upgrade path support compared with earlier Windows Server releases.
However, the existence of a supported upgrade path does not confirm that every application, driver, management agent, or server role on your system is ready for the upgrade.
Microsoft operating system support is only one part of the compatibility review.
In-Place Upgrade vs Clean Migration
Before upgrading, choose the deployment method.
There are two common approaches.
In-Place Upgrade
The existing Windows Server operating system is upgraded to Windows Server 2025.
The goal is to preserve the current server environment.
This may include:
- Installed applications
- Server roles
- Configuration
- Local settings
- Data
The server retains its existing workload rather than being replaced by a newly deployed system.
Clean Migration
A new Windows Server 2025 system is installed separately.
The required roles, applications, and data are then migrated from the old server.
The process may look like this:
Windows Server 2022
↓
Deploy new Windows Server 2025 system
↓
Configure required roles
↓
Migrate data or application workload
↓
Test the new server
↓
Redirect users or services
↓
Decommission the old server
A clean migration requires more deployment work.
It also creates a clear separation between the old and new operating system environments.
Neither approach is automatically correct for every server.
The decision depends on the workload.
When an In-Place Upgrade Makes Sense
An in-place upgrade can be practical when the existing server is healthy and the workload has been verified for Windows Server 2025.
Typical factors supporting an in-place upgrade include:
- The current Windows Server 2022 installation is stable.
- The server has no unresolved operating system corruption.
- Installed applications support Windows Server 2025.
- Hardware or virtual hardware meets the requirements.
- Required drivers are compatible.
- The server role supports the planned upgrade.
- A tested backup and recovery process exists.
- A maintenance window is available.
An in-place upgrade may also reduce migration complexity for a server with an application that has a large amount of local configuration.
For example, rebuilding an application server from the beginning may require:
- Application installation
- Service account configuration
- Certificates
- Scheduled tasks
- Firewall rules
- Local permissions
- Registry configuration
- Integration testing
If the application vendor supports an operating system in-place upgrade, preserving the existing configuration may be useful.
The important phrase is if the application vendor supports it.
Do not assume that Windows Server support automatically means the business application supports the new operating system.
When a Clean Migration May Be Better
A clean migration may be a better choice when the existing server has accumulated years of configuration changes or when the workload can be moved to a new system with controlled testing.
Consider migration when:
- The existing server has stability problems.
- Operating system corruption is suspected.
- Old drivers or management agents are installed.
- The server contains abandoned software.
- Application compatibility is uncertain.
- The hardware is also being replaced.
- The server role can be migrated cleanly.
- You want a simpler rollback path.
- The existing architecture needs to be redesigned.
A new Windows Server 2025 deployment gives the infrastructure team an opportunity to document what the workload actually needs.
An old server may contain:
- Disabled services from previous applications
- Old backup agents
- Legacy monitoring tools
- Forgotten scheduled tasks
- Temporary firewall rules
- Previous application versions
An in-place upgrade carries the existing environment forward.
Sometimes that is the main benefit.
Sometimes it is the main problem.
Do not use an operating system upgrade as a substitute for fixing an unhealthy server.
Check Windows Server Edition and Installation Type
Before starting the upgrade, document the current Windows Server configuration.
Check:
- Windows Server version
- Edition
- Installation option
- Activation and licensing state
- System architecture
For example:
Operating system: Windows Server 2022
Edition: Standard
Installation option: Desktop Experience
Architecture: x64
The target Windows Server 2025 installation media and edition must align with a supported upgrade path.
Do not assume every combination of editions and installation types can preserve applications and settings.
Server Core and Desktop Experience also require attention.
An existing Server Core installation should be evaluated against the appropriate target installation option.
Likewise, a server running Desktop Experience should use a compatible upgrade path.
Windows Server 2025 does not provide a normal post-installation conversion between Server Core and Desktop Experience.
If your goal is to change the installation option, plan a clean installation rather than treating the operating system upgrade as a GUI conversion method.
For installation option details, see our Windows Server 2025 Installation Guide.
Check Application Compatibility Before Upgrading
Application compatibility is one of the most important parts of server upgrade planning.
Create an inventory of installed business applications.
Do not rely only on the Programs and Features list.
Also review:
- Windows services
- Scheduled tasks
- IIS applications
- Database services
- Application directories
- Startup components
- Monitoring agents
- Backup software
- Security tools
For each critical application, confirm Windows Server 2025 support.
Check the application vendor’s documentation.
You may discover that the current application version supports Windows Server 2022 but requires an application update before it can run on Windows Server 2025.
The correct sequence may therefore be:
Update the application
↓
Verify application health
↓
Upgrade Windows Server
not:
Upgrade Windows Server
↓
Discover the application is unsupported
Compatibility should be confirmed before the maintenance window.
Review Server Roles
Document the Windows Server roles and features installed on the system.
Examples include:
- Active Directory Domain Services
- DNS Server
- DHCP Server
- Hyper-V
- File and Storage Services
- Web Server (IIS)
- Remote Desktop Services
Different roles may require different upgrade planning.
A standalone file server is not the same as a domain controller.
A Hyper-V host requires consideration of the virtual machines running on the system.
An RDS server may depend on:
- Session collections
- Applications
- User profiles
- RD Licensing
- Certificates
- Connection Broker configuration
Do not describe the system only as:
Windows Server 2022 Standard
The operating system edition does not tell you what the server actually does.
Document the role before choosing the upgrade process.
Create a Backup and Recovery Plan
A backup should exist before an operating system upgrade.
More importantly, the recovery process should be understood.
Ask:
- What is being backed up?
- When was the last successful backup?
- Has the backup job been reviewed?
- Where is the backup stored?
- How long would recovery take?
- Can the complete server be restored?
- Are application-specific backups required?
- Who will perform the recovery if the upgrade fails?
For a virtual machine, a hypervisor checkpoint or snapshot may appear to provide an easy rollback option.
Do not automatically treat a snapshot as a complete backup strategy.
Snapshots and checkpoints have platform-specific operational considerations and may not provide the same protection as a tested backup stored separately from the production workload.
For application servers, verify whether the application requires its own backup process.
A database application may require application-consistent backups.
A file server may require both data protection and configuration documentation.
A domain controller has Active Directory-specific recovery considerations.
The backup plan should match the server role.
Document the Existing Server Configuration
Before the upgrade, create a basic server record.
Include:
- Server name
- IP addresses
- DNS configuration
- Domain membership
- Installed roles
- Installed applications
- Windows services used by applications
- Storage volumes
- Shared folders
- Scheduled tasks
- Certificates
- Firewall rules
- Backup configuration
You do not need to manually copy every Windows setting.
The purpose is to create a reference.
If the upgraded server starts and an application cannot communicate with another system, the documentation helps answer:
What did this server look like before the upgrade?
Screenshots alone are not enough.
Record important configuration values as text where practical.
A simple pre-upgrade document can save hours of troubleshooting.
Prepare Windows Server 2022 for the Upgrade
Do not start Setup immediately after confirming the upgrade path.
Prepare the existing operating system.
Install Applicable Windows Updates
Bring the current Windows Server 2022 installation to a healthy servicing state according to the organization’s update process.
Restart the server if required.
Do not begin a major operating system upgrade with a pending restart from another update unless the upgrade documentation specifically accounts for that state.
Check Free Disk Space
The system volume needs sufficient free space for the upgrade process.
Review:
- C: drive free space
- Temporary files
- Old logs
- Crash dumps
- Application caches
Do not delete unknown files simply to create free space.
Identify what is consuming the storage.
Review Event Logs
Check for recurring critical errors.
Pay particular attention to:
- Disk errors
- File system problems
- Driver failures
- Application crashes
- Service failures
A server generating storage errors before the upgrade is not a good candidate for an immediate in-place upgrade.
Fix the underlying problem first.
Verify Server Health
Review the operating system and workload.
Can users access the service?
Are required Windows services running?
Are backups completing?
Is replication healthy where applicable?
Does the application start correctly?
You need a known baseline before the upgrade.
Otherwise, a pre-existing problem may incorrectly be blamed on Windows Server 2025.
Review Third-Party Security and Management Software
Endpoint security, backup agents, hardware management software, and monitoring tools can interact deeply with the operating system.
Confirm that installed versions support Windows Server 2025.
Follow the vendor’s upgrade recommendations.
Do not automatically uninstall security software without a deployment and recovery plan.
How to Upgrade Windows Server 2022 to Windows Server 2025
The following process describes a typical in-place upgrade using appropriate Windows Server 2025 installation media.
The exact screens and available options may vary according to edition, licensing channel, and current server configuration.
Step 1: Confirm the Backup
Before opening Windows Server Setup, confirm that the final pre-upgrade backup completed successfully.
Record the backup completion time.
If the workload uses an application-specific backup, verify that process as well.
Step 2: Sign In with Administrative Permissions
Sign in to Windows Server 2022 using an account with the permissions required to perform the operating system upgrade.
Close unnecessary applications and management sessions.
Notify users or application owners that the maintenance window has started.
Step 3: Mount the Windows Server 2025 Installation Media
Mount the appropriate Windows Server 2025 ISO or attach the approved installation media.
Use installation media appropriate for the server’s target edition and licensing channel.
Open the installation media from the existing Windows Server 2022 environment.
Do not boot from the installation media when your goal is to perform an in-place upgrade that preserves the existing server environment.
Run Windows Server Setup from the current operating system.
Step 4: Start Windows Server Setup
Launch Setup.
The installer performs initial checks and prepares the upgrade process.
Depending on the upgrade method and media, Setup may offer options related to updates or installation improvements.
Follow the organization’s change and update process.
Step 5: Select the Correct Windows Server 2025 Edition
Choose the Windows Server 2025 edition that matches the supported upgrade path and deployment plan.
Read the complete edition name.
Verify:
- Standard or Datacenter
- Server Core or Desktop Experience
Do not continue until the target selection has been confirmed.
If the expected option to preserve files and applications is unavailable, stop and investigate.
Do not choose a clean installation option simply because Setup does not offer the upgrade path you expected.
A missing preservation option may indicate an edition, language, installation type, or media mismatch.
Step 6: Accept the Applicable License Terms
Review the Microsoft Software License Terms presented by Setup.
Accept the terms if appropriate for the deployment and continue.
Step 7: Choose to Keep Files, Settings, and Applications
For an in-place upgrade, select the option that preserves the existing server environment when that option is available for the supported upgrade path.
The wording displayed by Setup may vary.
Review the selection carefully.
The purpose of the in-place upgrade is to preserve the compatible server configuration while changing the Windows Server version.
If Setup only offers a clean installation, do not continue until the reason is understood.
Step 8: Review Compatibility Warnings
Windows Server Setup performs compatibility checks.
Do not treat warnings as screens that need to be clicked through quickly.
Setup may identify:
- Incompatible applications
- Driver issues
- Unsupported configuration
- Required changes
Read each message.
If an application or driver blocks the upgrade, stop and resolve the compatibility issue.
The maintenance window is not the time to discover what an unknown storage or network driver controls.
Step 9: Begin the Upgrade
Once the compatibility review is complete, start the upgrade.
The server will restart multiple times.
The amount of time required depends on:
- Server performance
- Storage speed
- Installed applications
- Server configuration
- Upgrade method
Do not interrupt the server because a particular stage appears to take longer than expected.
Monitor the console or remote hardware management interface.
For physical servers, make sure out-of-band management access is available where possible.
Step 10: Sign In to Windows Server 2025
After Setup completes, sign in to the upgraded server.
Do not immediately declare the upgrade successful.
The operating system reaching the login screen confirms that Windows started.
It does not confirm that the server workload is healthy.
The post-upgrade verification begins now.
Verify the Server After the Upgrade
Use the pre-upgrade documentation as a checklist.
Confirm the Windows Server Version
Verify that the server is running Windows Server 2025.
Confirm the expected edition.
Review activation and licensing status according to the organization’s deployment process.
Check the Server Name and Network Configuration
Verify:
- Computer name
- Domain membership
- IP addresses
- Subnet configuration
- Default gateway
- DNS servers
Test DNS resolution and required network connectivity.
Check Windows Server Roles
Confirm that required roles are present and operating.
For example:
- DNS service
- DHCP service
- IIS
- File services
- Hyper-V
A role appearing as installed does not automatically mean the workload is healthy.
Test the service.
Check Business Applications
Open or test each critical application.
Verify:
- Windows services
- Application interfaces
- Database connectivity
- Scheduled jobs
- External integrations
Ask the application owner to perform a functional test where appropriate.
Review Event Logs
Check System and Application logs.
Some informational events and warnings may occur during an operating system upgrade.
Focus on recurring errors related to:
- Storage
- Networking
- Drivers
- Applications
- Services
Compare them with the pre-upgrade baseline.
Verify Backup Software
Confirm that the backup agent or service is running.
Run or monitor the next backup job.
A server upgrade should not be considered complete while the new operating system state remains unprotected.
Install Applicable Updates
Check for Windows Server 2025 updates according to the organization’s servicing process.
Restart the server when required.
Then perform another application and service check.
Upgrading Domain Controllers
Domain controllers deserve a separate upgrade discussion.
Although an in-place operating system upgrade can be supported in applicable scenarios, Microsoft recommends a migration-style approach for domain controller modernization: deploy a new server with the newer Windows Server version, promote it to a domain controller, and demote older domain controllers as appropriate.
A simplified process may include:
- Review Active Directory health.
- Verify replication.
- Review DNS.
- Deploy Windows Server 2025.
- Join the server to the domain.
- Promote it to a domain controller.
- Verify replication and services.
- Transfer required roles where planned.
- Demote the older domain controller.
This creates a cleaner operating system deployment and allows the new domain controller to be tested before the old system is removed.
Do not treat a domain controller like a generic application server.
Active Directory health should be reviewed before changing the domain infrastructure.
Upgrading Hyper-V Hosts
Hyper-V hosts also require workload planning before an operating system upgrade.
Document:
- Running VMs
- VM storage locations
- Virtual switches
- Network adapters
- Host management configuration
- Backup software
- Cluster membership
- VM mobility requirements
The host must restart during the operating system upgrade.
That means running virtual machines need an appropriate shutdown or migration plan.
For a standalone Hyper-V host, the maintenance window may require shutting down the guest VMs.
In a multi-host environment, workloads may be moved according to the virtualization design and supported operational procedures.
Licensing should also be reviewed if the infrastructure architecture changes.
Our Windows Server Hyper-V Licensing Guide covers Standard stacking, Datacenter virtualization rights, and multi-host planning.
Do not upgrade a Hyper-V host without knowing where its virtual machines will run during the maintenance period.
Common Windows Server Upgrade Problems
Keep Files and Applications Is Not Available
This can indicate a mismatch involving:
- Edition
- Installation option
- Language
- Installation media
- Supported upgrade path
Stop and review the current and target Windows Server configurations.
Do not continue with a clean installation by mistake.
Application Does Not Start After the Upgrade
Check:
- Application vendor support
- Windows services
- Event logs
- Database connectivity
- Required runtimes
- Firewall rules
Compare the application configuration with the pre-upgrade documentation.
Network Connectivity Changes
Verify the network adapter, IP configuration, gateway, DNS servers, and firewall.
For physical servers, review the network driver.
A Windows Service Is Stopped
Confirm whether the service is configured to start automatically.
Review service dependencies and Event Viewer.
Do not repeatedly start a failing service without identifying why it stops.
Server Performance Is Poor After the Upgrade
Review:
- CPU utilization
- Memory
- Storage latency
- Driver status
- Windows updates
- Security software
- Application behavior
Allow normal post-upgrade servicing tasks to complete, but investigate sustained performance problems.
Backup Jobs Fail
Verify that the backup software version supports Windows Server 2025.
Check the backup agent, credentials, services, and repository connectivity.
Do not leave backup failures unresolved after the maintenance window.
Windows Server 2025 Upgrade Checklist
Before the upgrade:
- Confirm the supported upgrade path
- Document Windows Server edition
- Document Server Core or Desktop Experience
- Review hardware requirements
- Check application compatibility
- Inventory server roles
- Review third-party drivers and agents
- Check server health
- Review event logs
- Confirm free disk space
- Install applicable updates
- Complete and verify backups
- Document network configuration
- Define the maintenance window
- Define the recovery process
During the upgrade:
- Use the correct Windows Server 2025 media
- Run Setup from the existing operating system for an in-place upgrade
- Select the correct edition and installation option
- Confirm the preservation option
- Read compatibility warnings
- Monitor server restarts
- Do not interrupt Setup unnecessarily
After the upgrade:
- Verify Windows Server 2025 version and edition
- Check activation status
- Verify network configuration
- Test DNS
- Check installed roles
- Test applications
- Review Windows services
- Review Event Viewer
- Verify backup software
- Install applicable updates
- Perform a final workload test
Frequently Asked Questions About Upgrading to Windows Server 2025
Can I upgrade Windows Server 2022 directly to Windows Server 2025?
Yes. Windows Server 2022 can be upgraded directly to Windows Server 2025 in supported configurations.
Does an in-place upgrade keep applications and data?
A supported in-place upgrade can preserve compatible settings, server roles, applications, and data. Compatibility and the selected upgrade path should be verified before deployment.
Should I perform an in-place upgrade or a clean installation?
It depends on the workload. A healthy, compatible application server may be a practical in-place upgrade candidate. A server with legacy software, stability problems, or a workload that can be migrated cleanly may benefit from a new Windows Server 2025 deployment.
Can I upgrade a domain controller to Windows Server 2025?
Supported upgrade scenarios exist, but Microsoft recommends deploying newer Windows Server domain controllers and demoting older domain controllers rather than relying on an in-place operating system upgrade as the preferred modernization approach.
Can I upgrade a Hyper-V host to Windows Server 2025?
Hyper-V host upgrades require planning for running VMs, storage, networking, cluster configuration, and maintenance downtime. Review the specific host environment before upgrading.
Why is the option to keep files and applications unavailable?
A mismatch in edition, installation option, language, installation media, or upgrade path may prevent Setup from offering the preservation option.
Do I need a backup before upgrading Windows Server?
A verified backup and recovery plan should be prepared before a production server operating system upgrade.
Can I use a VM snapshot as my only backup?
A snapshot or checkpoint should not automatically be treated as a complete backup strategy. Use a recovery process appropriate to the virtualization platform and server workload.
Should I update applications before upgrading Windows Server?
If the application vendor requires a newer application version for Windows Server 2025 support, update the application according to the vendor’s recommended sequence before the operating system upgrade.
How long does a Windows Server 2025 upgrade take?
Upgrade time depends on hardware performance, storage, installed applications, server configuration, and the upgrade method. Plan a maintenance window that includes both Setup and post-upgrade testing.
Final Thoughts
Upgrading Windows Server 2022 to Windows Server 2025 should begin with workload documentation, not Windows Setup.
A supported direct upgrade path exists, and an in-place upgrade can preserve compatible roles, applications, settings, and data.
That makes in-place upgrades useful.
It does not make planning optional.
Check the current Windows Server edition.
Document the installation option.
Inventory applications and server roles.
Confirm Windows Server 2025 compatibility.
Review server health.
Verify backups.
Understand how the server will be recovered if the upgrade does not complete successfully.
Then perform the upgrade.
After Windows Server 2025 starts, test the actual workload.
A login screen is not an application test.
A running Windows service is not proof that users can complete their work.
Verify networking, DNS, server roles, applications, scheduled processes, and backups before closing the maintenance window.
For hardware and compatibility planning, see our Windows Server 2025 System Requirements Guide.
If you are deploying a new server instead of upgrading an existing system, follow the Windows Server 2025 Installation Guide.
For virtualized environments, read the Windows Server Hyper-V Licensing Guide.
You can also return to the Complete Windows Server Licensing Guide for a broader overview of Windows Server editions, core licensing, CALs, and RDS.