Hitting the RDWeb server and opening a collection will take you to the gateway to process any conditional policies, then pass it to the broker for directing to the proper session host. But RDS is a bit different since it can use certificates that not all machines have. Go and read that article thoroughly. But, I’m not going to completely go off on a PKI best practices rant here…that’s for another day. Are they willing to accept the additional risk? If you are receiving an error message "Your computer can't connect to the Remote Desktop Gateway server. Granted, current versions of the Remote Desktop Client combined with TLS makes those types of attacks much more difficult, but there are still risks to be wary of. Contact your network administrator for assistance." I am having an issue connecting to servers through an rdp gateway. Just remember the principals are the same. Sure, it works…but guess what? I'd focus on leveraging a SAN certificate that contains all the FQDNs of the RDS Servers. To confirm the cause for this error, in the Remote Access Management console, in Step 2 Remote Access Server, click Edit, and then in the Remote Access Server Setup wizard, click OTP Certificate Templates. A fellow colleague of mine, Jacob Lavender(PFE), wrote a great article on how to remove self-signed RDP certificates…so if you’re wanting the details on how you can accomplish this, check out this link! Think of a Root CA Certificate and the chain of trust. To get rid of the RDP error message for connecting to Windows-based computers where you already have Microsoft PKI (or some other internal PKI), it seems to me that the most effective method of eliminating the warning would be to simply add the RDP OID ("1.3.6.1.4.1.311.54.1.2" for the "Enhanced Key Usage") to an existing device/computer certificate that your PKI is already issuing to computers/devices, if you are already pushing out certificates for computers. But hey, I’m sure wherever you are it’s nice there too. For Single Sign On, the subject name needs to match the servers in the collection.”. We have purchased a wildcard certificate for *.acme.com from a public CA which we should be able to use for machines on our internal domain. Then they can avoid the prompt. Talk about a management overhead nightmare! For example, for Publishing, the certificate needs to contain the names of all the RDSH servers in the collection. Simply double-click the . Microsoft has made the needed certificate store parts available but has developed no way to utilize them with Microsoft PKI, auto-enrollment, or GPOs (outside of the Computer certificate store, short of running scripts and using registry keys). Unless there are security requirements that they must meet, most organizations don’t deploy certificates for systems where they are simply enabling RDP to allow remote connections for administration, or to a client OS like Windows 10. Proof:  In my lab, I got a warning message since I tried to RDP to an IP . However, if RDP using names still produces warning messages then let’s continue. ... On the RD Connection Broker server, obtain the certificate used for Remote Desktop connections and export it as a .cer file. Remote Desktop Services rely on having a valid certificate being used by all the services on all servers, or to have a self-signed certificate that is pushed to all workstations that will be used so the connection is trusted. These powerful SSL tools deliver instant scans and reports on the state of your SSL Certificate. Here in the fall, in the Ozark Mountains area the colors of the trees are just amazing! Stack Exchange Network. Okay this scenario is a little like the previous one, except for a few things. Contact your network administrator for assistance." In this instance, all users and machines can be configured to automatically enroll for a certificate, barring a published template’s permissions are set correctly. Otherwise, register and sign in. After update my Windows 10 to creators update (1703), it's not possible to connect a server in RDP with Remote Desktop Gateway (RDG). The behavior you 're inquiring about is a little like the previous one, except for a RDP... Assume that whoever is reading this correctly, you 're inquiring about is a bit since. Computers are properly authorized in the first place now and am accessing the server keeps enrolling a... 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