I realize the following will not get much attention within Esri Community because most Esri Community members are not on the IT service delivery side of GIS, but change has to start somewhere....
Still in 2025 with ArcGIS Enterprise 11.5, installing ArcGIS Server requires the 'Desktop Experience option' on Windows Servers. From ArcGIS Server 11.5 system requirements - ArcGIS Enterprise | Documentation for ArcGIS Enterprise:
Note:
- The Desktop Experience option is required on all versions of Windows Server.
Why oh why is Desktop Experience still required with Windows Server installations after 17 years since Microsoft introduced Server Core with Windows Server 2008?
Infrastructure as code (IaC) is far from a new idea, and Esri already supports several automated on-premises deployment patterns (script-based silent installation, Chef cookbooks, PowerShell DSC), so it is time for Esri to remove a Desktop Experience requirement for a product that does not require a GUI to deploy, configure, and manage.