Upgrading from Windows Server 2012 R2 to Windows Server 2019 Essentials is a bit of a unique situation. Here’s what you need to know: 1. Direct Upgrade Path: Windows Server 2012 R2 can be upgraded directly to Windows Server 2019, but not from a corresponding edition of Essentials. The upgrade path typically moves from Standard to Standard or Datacenter to Datacenter. Essentials is a specialized edition designed for small businesses. 2. Migration vs. Upgrade: Since you are moving from a standard version of 2012 R2 to Essentials in 2019, you will need to consider a migration rather than a direct upgrade. This means that while you can retain your data, the server settings, RDP, and users will likely need to be reconfigured on the new server. 3. User Limitations: As you mentioned, your user count is less than 25, which is within the limit for Essentials. However, you should prepare for the migration by backing up your data and documenting your current server settings and user configs. 4. Recommendations: - Backup: Ensure that you have comprehensive backups of your server, including user data and configurations. - Plan Migration: Look into comprehensive migration tools or services that can help migrate users, settings, and data to the new Essentials environment. - Documentation: Document your current setup—user accounts, RDP configurations, and any other custom settings. 5. Testing: If possible, set up a test environment to simulate the migration process. This will help identify any issues and familiarize you with the setup. In summary, while you can't upgrade directly to Essentials, with proper planning and backup, you can migrate smoothly to Windows Server 2019 Essentials. If you have further questions or need detailed steps for the migration process, feel free to ask!