Operations | Monitoring | ITSM | DevOps | Cloud

Notes from the Field: Seamless SSO 404s Impacting Citrix on Windows Server 2025

As a Citrix consultant, not every issue I troubleshoot is directly tied to Citrix, but many of them dramatically impact the end-user experience. This is one of those cases. A customer had begun testing Windows Server 2025 as Multi-Session hosts in their environment. The new servers were domain-joined and fully patched, and they expected a smooth experience with Office 365, Entra ID–backed apps, and cloud-based authentication. Everything had worked flawlessly on Server 2022.