Hi KylanWong,
The error "Unable to contact Active Directory to access or verify claim types" occurs because the Windows GUI "Object Picker" (the interface you use to search and add users) operates locally on the client machine. It attempts to query the Domain Controller directly via LDAP and RPC to translate the username into a Security Identifier (SID) before applying the permission. Since your Workgroup VM is isolated and cannot reach the DC, this translation process fundamentally breaks.
Because the local GUI relies on direct DC access, you cannot bypass this from the Workgroup VM's visual interface. You must shift the execution context to the File Server (which does have DC access). Here are the two most viable administrative approaches for your isolated environment:
- PowerShell Remoting (Native & Scriptable)
Your system administrator can add the folder owners (like User A) to the Remote Management Users group on the File Server. This allows User A to open PowerShell on their Workgroup VM and establish a secure remote session directly to the File Server by running: Enter-PSSession -ComputerName <FileServer_IP> -Credential (Get-Credential)
Once connected, the shell runs in the context of the File Server. User A can then seamlessly assign permissions using standard command-line tools, as the File Server can easily contact the DC to resolve the names: icacls "D:\Shares\TargetFolder" /grant "Domain\UserB:(OI)(CI)M"
- A Domain-Joined Jump Box or RemoteApp (GUI Friendly)
If your users are not comfortable with command-line tools, the most secure and standard enterprise workaround is to deploy a lightweight, domain-joined "Management VM" or RDS server within the secure network zone. You can publish "Windows Explorer" as a RemoteApp. Users on the Workgroup VMs can launch this RemoteApp (authenticating with their domain credentials). Since the application is running on a domain-joined machine, the GUI Object Picker will work perfectly, allowing them to right-click and manage permissions visually as usual.
I hope this answer provided you with useful information. If so, please click "Accept Answer". If you have any questions, do not hesitate to leave a comment.
Tracy Le.