Azure Automanage currently does not support virtual machines that use the Trusted launch security type; this is an explicit, documented limitation of the service, independent of which Windows Server version or edition the VM is running. Looking at the four virtual machines ' security types, Server1 (Windows Server 2022 Datacenter: Azure Edition) and Server4 (Windows Server 2019 Datacenter) are both configured with Trusted launch, which makes both of them ineligible for Automanage onboarding regardless of their OS version. Server2 (Windows Server 2022 Datacenter: Azure Edition) and Server3 (Windows Server 2022 Datacenter) both use the Standard security type and run OS versions on Automanage ' s supported list, so both qualify and Automanage should be enabled on them to satisfy the requirement that it be used on " all supported " virtual machines, which by definition excludes the ones the service cannot onboard. It is a common misreading of this scenario to assume the Azure Edition label is the deciding factor, since Server1 and Server2 share that edition; the actual determining attribute the requirement hinges on is the VM ' s security type, not its Windows Server edition. Therefore Server2 and Server3 are the correct machines on which to enable Automanage.