1. Policy setting "always prompts for a password upon connection" in Computer configuration\Administrative templates\Windows components\Remote Desktop Service\ Remote Desktop Session Host\Security 2. fPromptForPassword registry value in HKEY_LOCAL_MACHINE\SOFTWARE\Policies\Microsoft\Windows NT\Terminal Services Is it possible that some other settings override local policy?

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Hi, Only registry setting will override the local policy. However, if you are in domain, domain group policy is priority. Best Regards, NikiPlease remember to click "Mark as Answer" on the post that helps you, and to click "Unmark as Answer" if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.