Transparent Login is being configured in Privileged Access Manager (PAM), but the learn tool window cannot open in learn mode.
PAM requires drive redirection in order to mount a temporary drive that contains the learn tool files. If the following group policy is set to Enabled, the learn tool cannot run.
Computer Configuration\Policies\Administrative Templates\Windows Components\Remote Desktop Services\Remote Desktop Session Host\Device and Resource Redirection
Log into the target Windows server as an administrator and set the policy to either Disabled or Not Configured and run the learn tool again. This change does not require a reboot.