This occurs from the RDWeb site as well as from the RCP client. network. This behavior is most likely to occur if your domain controllers are running Windows Server 2016 or later, and users attempt to connect by using a customized connection ... To enable the legacy RCM behavior on a RD Session Host server, ... Users are denied access on a deployment that uses Remote Credential Guard with multiple RD Connection Brokers. I don't have Exchange installed anywhere. This makes it frustratingly slow to analyse this problem. It's Remote Desktop that doesn't work externally, whether I try by accessing a server link from the Remote Web Access home page or by running the Remote Desktop Connection client. After enabling this option, login errors went away. It might be really helpful if I know more about how the requests are routed from IIS to RDG. When I attempt to Remote Desktop to the Essentials server, I get a Windows Security dialog saying: RD Gateway Server Credentials Type your user name and password to connect to . *OR* you can write code to "fancify" this. Launch Server Manager. Press Windows Key + R combination, type Firewall.cpl in the Run dialog box and hit Enter to open the Windows Firewall. We have a terminal server farm configured with a few RDS session hosts, and a gateway server. The log is located in “Windows -> Security”. In the middle pane (the settings area), double-click HTTP Redirect . 2.In the IIS navigation tree, expand the server and the sites, and then select Default Web Site. not so? However, secondary login to the actual Remote Desktop Gateway fails with error: The issue was cased by incorrect Default Web Site HTTP redirect on the Windows Server 2012 (IIS Manager). Thanks again for replying. Meanwhile, please open Event Viewer and check if find some relevant events or errors. You have 2 settings. Based on your description, I noticed that you use two different types of user accounts. Surely SSL is encrypted so it would be very hard to block some traffic, such as RDP, whilst allowing other traffic, such as HTTP. The terminal services gateway must be part of an Active Directory domain. The logon attempt failed for Remote Connections. One thing really intrigues me, and it might give a clue to somebody who really knows how these things work. In the IIS navigation tree, expand the server and the sites, and then select Default Web Site. When I browse externally and examine the certificate, it is the correct externaldomainname certificate that was obtained from a trusted third party and previously worked Some setting in Active Directory perhaps; it's the only thing I can thing would have survived the creation of  new VM. I'm assuming that's the same password t I put in the login window when the computer boots up. Every attempt to enter credentials fails, whether I prefix the username with the domain name or not. It still works, even if I uncheck "Bypass RD Gateway server for local addresses", which is really annoying, but makes me think that somehow the external requests are not even getting as far as the remote desktop gateway but are being rejected in It's as though the autentication failure occurs before the gateway manager. The hosts file thing is so you can test at home and not get a cert error. Using them, you can assign monitored events for auditing, such as failed attempts to connect to the terminal services gateway server. I need someone to help me figure out why the TS gateway we have been using to enable our employees gain remote access for quite some time is no longer functional. I get a Windows Security dialog saying: RD Gateway Server Credentials Type your user name and password to connect to . I'm the only user and that's my name. 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