This will install the machine’s certificate accordingly on the local machine, so the next time you RDP using the remote machine’s name, the warning vanishes. I can now no longer connect to the servers behind that gateway. PRO TIP:  For most scenarios where the client is not domain-joined but connecting via RDP to a machine that IS domain joined you should probably be using an RD Gateway…since in those scenarios the client is coming in externally anyways. But RDG doesn't support Kerberos auth, only NTLM. Your computer can't connect to the remote computer because no certificate was configured to use at the Remote Desktop Gateway server. Remote Desktop Connection (RDP) - Certificate Warnings. Where certificates are deployed is all dependent upon what your environment requires. Contact your network administrator for assistance." This set the Certificate Level as "trusted" with a status as "ok" for all four role services. Meaning, they'll need to have the Root CA cert and any issuing CA cert installed locally. To mitigate the CA from handing out a ton of certs from multiple templates, just scope the template permissions to a security group that contains the machine(s) you want enrollment from. Make a note of the certificate template used for the enrollment of certificates that are issued for OTP authentication. The idea is to get rid of the warning message the right way…heh. I've been unable to correct this setting as well. But that's ok, I can point you in the right direction to start. A technicality, I admit, but Microsoft has had many years to properly develop these PKI pieces. Solution for this scenario – Export the remote machine’s certificate (no private key needed) and create a GPO that disperses the self-signed certificate from the remote machine to the local machine. SAN entries are used, not the CN of the certificate. 09/08/2020; 4 minutes to read; D; s; In this article. You will always get the warning because you are trying to connect using IP address instead of a name, and a certificate can't be used to authenticate an IP address. But, I’m not going to completely go off on a PKI best practices rant here…that’s for another day. Facebook; Twitter; LinkedIn; https://www.experts-exchange.com … But RDS is a bit different since it can use certificates that not all machines have. (https://technet.microsoft.com/en-us/library/ff458357.aspx). Go and read that article thoroughly. The client machine you’re trying to establish the RDP session from doesn’t have the remote machine’s self-signed certificate in the local Trusted Root CA certificate store. Sure, it can be perceived as a hassle sometimes, but dog gone it…don’t just click through it without reading what it’s trying to tell you in the first place! When configuring a new template with the Remote Desktop Authentication EKU, is it necessary to tick the option to Publish to Active Directory? I am writing this blog post to shed some light on the question of “How come we keep getting prompted warning messages about certificates when we connect to machines via RDP?”  A couple of examples you might see when running the Remote Desktop Connection Client (mstsc.exe)…. If you are receiving an error message "Your computer can't connect to the Remote Desktop Gateway server. The DNS A Record we use I'm assuming is our farm name (one name pointed to all the SH's IP addresses). If your managing that server it is on you. Doesn’t matter…or does it? So how do we remedy that? You will need the thumbprint of the certificate you wish RDP to use, and the cert itself must exist in the machine’s personal store with the appropriate EKU. Initial issue was that there "was a problem with the remote computer" I added this DWRD "RDGClientTransport" to the registry and set the value to 1 on the client PC. On the Connection Broker, open the Server Manager. Think of a Root CA Certificate and the chain of trust. Hello everyone! I’m going to go through a few scenarios where the warning messages can be displayed, and then how you can remediate them THE SUPPORTED WAY. I updated group policy on a member server, and tested it. So when using MSTSC.EXE on the outside, we get prompted about the certificate. Here’s an example:  In my lab, a custom certificate with the Remote Desktop Authentication EKU was installed via autoenrollment. Begin with this article here -https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2012-R2-and-2012/dn... Keep in mind on how RDS works. Told you it was cool! @NikkiAIT are you still having issues with this? The hotfix has a prerequisite. If you’ve come across this in your environment, don’t fret…as it’s a good security practice to have secure RDP sessions. You add more risk that way. Again, we use certificates to maximize security pertaining to Remote Desktop Connections and RDS. You must be a registered user to add a comment. (not user). You can enhance the security of RD Session Host sessions by using Secure Sockets Layer (SSL) Transport Layer Security (TLS 1.0) for server authentication and to encrypt RD Session Host communications. In your deployment properties, are all the certificates showing as "trusted"? Microsoft wants you to be warned if there’s a potential risk of a compromise. Only the RD Web Access and RD Gateway roles should ever be exposed to the Internet, which means obtaining a certificate for those roles from a Public CA. In your case, you're talking about the Machine's Personal store...which is different from the RDP store. You don’t have to manually do anything to each individual server in the deployment! Regarding point (A), there appears to be no way to automate a certificate install to that node in the Computer certificate store. Otherwise you’ll get warnings despite the fact the cert is deployed in the local Trusted Root CA store. "Your computer can't connect to the remote computer because the Remote Desktop Gateway server's certificate has expired or has been revoked. We help IT Professionals succeed at work. The Enhanced Key Usage extension has a value of either “Server Authentication” or “Remote Desktop Authentication” (1.3.6.1.4.1.311.54.1.2). Connecting To Your Server Using Remote Desktop Protocol (RDP) "Your computer can't connect to the remote computer because the Remote Desktop Gateway Server's certificate has expired or has been revoked. One little caveat though:  Certificate SAN names for CNAME DNS entries. RDP is doing the same thing. Find out more about the Microsoft MVP Award Program. Furthermore, when you look at the self-signed certificate, it only has the "server authentication" enhancement, not the RDP OID. Just remember the principals are the same. Remote Desktop Services (RDS) is one of the components of Microsoft Windows that allow users to access a remote computer or virtual machine over a network connection. Just take the time to plan / lab things out before deploying to production…. Quick shout out to my buds SR PFE Don Geddes (RDGURU), and PFE Jacob Lavender who provided some additional insight on this article! Original product version: Windows Server 2012 R2 Original KB number: 3042780. wmic /namespace:\\root\cimv2\TerminalServices PATH Win32_TSGeneralSetting Set SSLCertificateSHA1Hash="THUMBPRINT", $path = (Get-WmiObject -class "Win32_TSGeneralSetting" -Namespace root\cimv2\terminalservices -Filter "TerminalName='RDP-tcp'").__path, Set-WmiInstance -Path $path -argument @{SSLCertificateSHA1Hash="THUMBPRINT"}. What I mean is that there is (A) a node in the Windows Computer Certificate store for the self-signed certificate which is specific to the "Remote Desktop Services" service on Windows-based OS's which is automatically used for RDP, and (B) there is a certificate store specific to services running on the OS platform, and specifically for the "Remote Desktop Services" service. Tim Beasley, Platforms PFE here again from the gorgeous state of Missouri. Contact your network administrator for assistance." Now we get to the meaty part (as if I haven’t written enough already). The option you want to set is “Server Authentication certificate template.”  Simply type in the name of your custom certificate template, and close the policy to save it. If you continue to have issues in this particular situation, I advise you open a case with CSS. 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! Fixes an issue in Windows Server 2008 R2 in which some IIS clients cannot connect to the Remote Desktop Gateway service. Once the template’s created and scoped appropriately via permissions (autoenrollment or whatever) then it’s time for the machine to request the certificate. thanks for detailed explanations.i.e. The catch is that you must do it from the individual machine. The name you’re trying to connect to must exist on the certificate! But this, technically, doesn't place an RDP certificate in the correct, more "correct" place. How do we do that? The GPO settings are located under: Computer Configuration, Policies, Administrative Templates, Windows Components, Remote Desktop Services, Remote Desktop Session Host, Security, Server Authentication certificate template. That resolved that issue but now i get "The remote desktop gateway server's certificate is expired or has been revoked. Warning went POOF! Let’s say Remote Desktop Services has been fully deployed in your environment. I manually verified if certificate is revoked, seems like certificate is not revoked but CA is giving a generic message of expired certificate… This is particularly prevalent with the default user template. I don’t know how many users are out there that believe that this method is correct. But I can't replace the certificate until I can remote in. Next step, open RD Gateway Manager, right-click the server’s name and choose Properties. Manual = no built in automation, hence why I also mentioned scripting via PowerShell. Sure, it works…but guess what? No need to push out a new certificate template. RDP - 'Your computer can't connect to the remote computer because the Remote Desktop Gateway Server's certificate has expired … The root cert is in there .... that won't cause a problem, will it? You still must connect using the correct machine names. The roles themselves handle all that. This article describes the methods to configure listener certificates on a Windows Server 2012-based or Windows Server 2012-based server that is not part of a Remote Desktop Services (RDS) deployment. Regarding point (B), there is no strictly GPO-based method of getting a special certificate into the certificate store for the "Remote Desktop Services" service. Choose the option that fits your business needs...what does your security team say? Community to share and get the latest about Microsoft Learn. It was working perfectly fine until the rdp gateway certificate expired back in December. First published on TechNet on Dec 18, 2017. I’m also going to assume that whoever is reading this knows a bit of PKI terminology. Here in the fall, in the Ozark Mountains area the colors of the trees are just amazing! You can of course, but typically not mandatory. I was hoping for some input on our deployment... we are not using internal PKI for the RDS farm. Simply double-click the . Remote Desktop listener certificate configurations. You don't have an internal PKI, then use the self-signed certs...and, If you do have an internal PKI, then replace the self-signed certs using GPO and custom certs for the RDS service to use...and. DO NOT JUST HACK THE REGISTRY TO PREVENT WARNING PROMPTS FROM OCCURRING. *stifles laughter*. Any advice? Now, when I visit our deployment from an external host (https://rdp.acme.com/rdweb) and RDP to one of my host collections, I still receive a certificate error from the broker--it shows that "broker.acme.com" is still using a self-signed certificate. See! That's why I'm trying to get in to fix it! Contact your network administrator for assistance." Click Remote Desktop Services in the left navigation pane. I would think that PKI specialists would want the service to have the certificate rather than the computer account. Seems like when RDS tries to access company file, QB is validating the digital signature certificate with its issuer to check if certificate has been revoked. Auto-suggest helps you quickly narrow down your search results by suggesting possible matches as you type. Her article details RDS certificates for Server 2008 R2, GPO settings, etc. 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. I assume your Session Hosts, since you stated the web access is presenting the self-signed cert for the Session Hosts rather than your wildcard. Please help! I'm trying to setup Remote Desktop Gateway (Terminal Service Gateway) on virtual Windows Server 2012 R2. Connect with Certified Experts to gain insight and support on specific technology challenges including: We've partnered with two important charities to provide clean water and computer science education to those who need it most. However, this is a problem because we have terminal clients connecting (so they act more like a Windows PC using MSTSC.EXE). For example, for Publishing, the certificate needs to contain the names of all the RDSH servers in the collection. Proof:  In my lab, I got a warning message since I tried to RDP to an IP . The RD Session Host server and the client computer must be correctly configured for TLS to provide enhanced security. Import remote machine’s certificate into a new GPO at Computer Configuration -> Policies -> Windows Settings -> Security Settings -> Public Key Policies -> Trusted Root Certification Authorities. remote desktop gateway certificate expired or revoked windows 7 Can anyone point me in the right direction as to what I’m doing wrong. You can also use certificates with no Enhanced Key Usage extension. If the session hosts are handing out their self-signed certs rather than the wildcard cert in your deployment properties, there's a problem in your configuration somewhere. I bet you could script it via PowerShell to speed things up a bit, but still more-so a manual thing. Neither can Kerberos for that matter. Just because it’s trusted doesn’t guarantee warnings are forever gone. 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. The certificate is installed in the local computer’s “Personal” certificate store. Otherwise, register and sign in. Remote Desktop Gateway history and versions. Thank you for taking the time to read through all this information. RDP - "Your computer can't connect to the remote computer because the Remote Desktop Gateway Server's certificate has expired or has been revoked. Why not you ask? This is the cool part! I am outside the office now and am accessing the server remotely. And given that, often customers are typing in domain admin credentials…which means you could have just given an attacker using a Man-in-the-Middle (MTM) attack the keys to the kingdom. I tried to think of all the scenarios I personally have come across in my experiences throughout the past 25 years, and I hope I didn’t miss any. 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). I realize this is perhaps geared more toward Terminal Services, but for Windows systems, I would assert this is not, technically, the proper setup. I then created a GPO called “RDP Certificate” and linked it at the domain level. And because of this, it's giving a unknown computer as the cert being presented is an internal cert, not the public cert and DNS we are using. In Windows 2012 / 2012R2, you connect to the connection broker, and it then routes you to the collection by using the collection name. From a security / PKI perspective wildcard certs aren't generally recommended. ... On the RD Connection Broker server, obtain the certificate used for Remote Desktop connections and export it as a .cer file. Experts Exchange always has the answer, or at the least points me in the correct direction! If only it was that easy! If so, make sure the wildcard SAN is correct. If you use CNAME (alias) DNS records in your environment, DO NOT try and connect to a machine using the CNAME entry unless that CNAME exists on the certificate. Referring to the methods mentioned in the following information is from this TechNet Article: “In Windows 2008 and Windows 2008 R2, you connect to the farm name, which as per DNS round robin, gets first directed to the redirector, then to the connection broker, and finally to the server that hosts your session. Kerberos plays a huge role in server authentication so feel free to take advantage of it. Windows - "Your computer can't connect to the Remote Desktop Gateway server. Click Select existing certificates, and then browse to the location where you have a saved certificate (generally it’s a .pfx file). Read the following sections, or pick which one applies for your situation: I’m going to begin this by saying that I’m only including this scenario because I’ve come across it in the past. Your clients want to use/trust certificates that a CA issues, but they must trust the certificate authority that the certificates come from, right? Windows is trying to make RDP secure, doing all sorts of mutual authentication things with x.509 certificates. Certificate contents. READ MORE. By default, RD Session Host sessions use native RDP encryption. Hi Will! Technically speaking, your wildcard certificate should be fine as long as the *.acme.com entry is in the SAN field...AND...the internal FQDNs of servers are also acme.com. The Kerberos authentication protocol provides a mechanism for authentication — and mutual authentication — between a client and a server, or between one server and another server. (There’s several articles that walk you through this process if you haven’t done so already - here and here). 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. ADCS - https://gallery.technet.microsoft.com/Windows-Server-2016-Active-165e88d1, RDS Farm - https://gallery.technet.microsoft.com/Windows-Server-2016-Remote-ffc383fe. In regards to the renewal during reboot scenario, this would happen if you have a cert lifetime that's extremely short (more likely your case) or have a renewal period that spans the GPO refresh cycle. Click Tasks > Edit Deployment Properties. But if the end users are constantly being prompted, then it sounds like those users don't trust the chain that wildcard certificate came from. I can’t tell you how many times we’ve seen customers manually change registry settings or other hacks to avoid the warning prompts. The obvious problem is that it's saying we're logging into "ext-gwname.domain.com" and "int-shname.domain.com". It kind of bothers me that I get a certificate warning when I RDP into my non-domain-bound offline root CA. Once I’ve got the .pfx file, I copied it over to the Gateway server and imported it to the local computer’s certificate repository. Furthermore, I have configured the deployment to use "rdp.acme.com" as the RD Gateway server name, yet when I log in to RDWeb and click on a collection, the RDP session lists the "remote computer" as "broker.acme.com" (correct) and the "gateway server" as "gateway.acme.com" (incorrect; this should be rdp.acme.com). 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