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The "Automatic connection" error typically occurs when the RD Licensing Manager cannot communicate with the Microsoft Clearinghouse over TCP port 443. This is commonly caused by strict network firewalls, unauthenticated proxy servers, or disabled TLS 1.2 protocols on the Windows Server. On the other hand, the inability to install Per-User CALs via the Web Browser method usually happens if there is a mismatch in the License Program selected (e.g., Enterprise Agreement vs. Retail Purchase) or if the generated Key Pack ID isn't entered correctly into the wizard.
To resolve the issue, first ensure that your network firewall allows outbound HTTPS (port 443) traffic from the RD Licensing Server to activate.microsoft.com. If your network allows the traffic, you may need to enforce TLS 1.2, especially if you are running an older OS like Windows Server 2012 R2 or Windows Server 2016. You can enforce TLS 1.2 by running the following PowerShell commands as an Administrator:
New-Item 'HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server' -Force
New-ItemProperty -Path 'HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server' -Name 'Enabled' -Value 1 -PropertyType 'DWord' -Force
New-ItemProperty -Path 'HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Server' -Name 'DisabledByDefault' -Value 0 -PropertyType 'DWord' -Force
New-Item 'HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client' -Force
New-ItemProperty -Path 'HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client' -Name 'Enabled' -Value 1 -PropertyType 'DWord' -Force
New-ItemProperty -Path 'HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client' -Name 'DisabledByDefault' -Value 0 -PropertyType 'DWord' -Force
Set-ItemProperty -Path 'HKLM:\SOFTWARE\Microsoft\.NETFramework\v4.0.30319' -Name 'SchUseStrongCrypto' -Value 1 -Type DWord
Set-ItemProperty -Path 'HKLM:\SOFTWARE\WOW6432Node\Microsoft\.NETFramework\v4.0.30319' -Name 'SchUseStrongCrypto' -Value 1 -Type DWord
Note: Modifying the registry can have system-wide effects. Please restart your server after applying these registry changes for them to take effect securely.
If network restrictions mean the automatic method is definitively blocked, you can use alternative offline methods to install the CALs.
To properly install CALs, right-click your server in the RD Licensing Manager, select Install Licenses, and verify the connection method is set to Web Browser in the server properties. The wizard will display your License Server ID. From any device with internet access, navigate to https://activate.microsoft.com, select Install Client Access Licenses, and provide your License Server ID along with the exact License Program details. Once you complete the prompts, you will receive a License Key Pack ID. Type this ID back into the RD Licensing Manager wizard to install the CALs.
For more details on these processes, you can review the official Microsoft documentation on how to Activate the Remote Desktop Services license server and Install RDS Client Access Licenses on the Remote Desktop license server.