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I have a Windows machine which I run headless (no monitor or keyboard). I control it by Remote Desktop. But whenever it reboots (for Windows updates and such), the RDP won't work until I log in physically. It's annoying; any way to have the RDP client (or whatever is necessary to enable remote login) start immediately on boot-up? Another option is to have it log me in as a user automatically, and I may do that (the computer is in my home and so under physical control) but it's not ideal - would be safer I guess to just have it run RDP and force the user to present credentials, rather than simply logging in into an account. How to make that happen?

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  • This can be achieved with Teamviewer. But i'm not sure acout RDP. I believe you'll need to have the user account automatically login.
    – NiallUK
    Commented Jun 21, 2019 at 11:02
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    @NiallJones: The odd thing about this problem is that RDP always performs the login on its own (unlike Teamviewer/VNC/etc, which have to use an existing login).
    – grawity_u1686
    Commented Jun 21, 2019 at 11:03
  • @grawity you're right. I didn't think of that.
    – NiallUK
    Commented Jun 21, 2019 at 11:04
  • The problem isn't with RDP. It is always available automatically... In fact, it's possible to connect via RDP to a machine before logon is possible. It's likely that logging in at the console is changing something with your network connectivity, ie connecting you to a user-based 802.1x authenticated network, or loading an internet filtering application etc. What do you have on the machine that's blocking inbound connections until you logon?
    – I say Reinstate Monica
    Commented Jun 21, 2019 at 11:29
  • You should be able to login to the console rather than on user level, which is the failsafe way. Connect to your ip address and append /admin. For example: server address: 192.168.0.1 /admin
    – LPChip
    Commented Jun 21, 2019 at 18:20

2 Answers 2

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I was having the same issue, connecting my Macbook to Windows 10 RDP. After I turned on the Windows machine, I first needed to login into it, before I could activate the RDP connection (using the same account).

After disabling the option "Allow connections only from computers running Remote Desktop with Network Level Authentication (recommended)" from the advanced RDP settings in Windows, the problem was resolved.

Note: when using Jump Desktop as a client, also disable the "Use Network Level Authentication" setting in the client configuration.

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Set the service "Remote Desktop Services" startup type to automatic ?

For Automatic Login you can set directly in the registry:

Navigate to or create this folder:

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Winlogon

Create 3 REG_SZ keys

 - AutoAdminLogon set to 1
 - DefaultUserName set to <username>
 - DefaultPassword set to <password>

You may need DefaultDomainName set if it's on a domain.

If you have enterprise you can set these in Group Policy objects here:

Computer Configuration > Preferences > Windows Settings > Registry
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