Windows 10 Enterprise EOL: Planning Your Windows 11 Migration on Amazon WorkSpaces
Options for migrating to Windows 11 WorkSpaces and considerations such as timeline and technical guidance.
Published Feb 28, 2025
Last Modified Mar 4, 2025
On October 14, 2025, Microsoft will end support for Windows 10 Enterprise, requiring organizations to transition to Windows 11 to maintain security compliance and support. For businesses using Amazon WorkSpaces, this transition requires careful planning, especially for those using Windows 10 Bring Your Own License (BYOL) deployments.
- Preparation Steps:
- Take inventory of WorkSpaces using the AWS Management Console
- Create a Windows 11 BYOL image
- Validate hardware specifications meet Windows 11 requirements
- Backup user data
- Migration Process:
- Create migration groups in WorkSpaces Migrate
- Schedule migration windows during off-hours
- Execute migration in batches of 50-100 WorkSpaces
- Monitor migration progress through WorkSpaces Migrate dashboard
- Post-Migration Tasks:
- Verify application functionality
- Confirm user profile integrity
- Validate group policy applications
- Run Windows updates
- Directory Configuration:
- Create new WorkSpaces Directory in AWS Directory Service
- Configure group policies for Windows 11
- Set up organizational units
- User Provisioning:
- Create Windows 11 WorkSpaces
- Establish permission structures
- Data Migration:
- Allow users a transition period to access Windows 11
- Transfer user settings & install apps
- Cutover Strategy:
- Schedule department-by-department transitions
- Maintain temporary access to both environments
- Decommission Windows 10 WorkSpaces after successful transition
While Windows 10 Enterprise EOL presents challenges, it also offers an opportunity to modernize your virtual desktop infrastructure. By starting early and following a structured approach, organizations can successfully transition to Windows 11 on Amazon WorkSpaces with minimal disruption.