One thing I quickly tired of was needing to remember to bind the new certificate to the service, lest the server restart and my users get a message about no certificate being bound to the service. Please follow the steps in order for best results….! Andrei, your posts are awesome! Required fields are marked *. Then ensure that the you configure external DNS with the FQDN required and ensure ports 443/3391 and port 80 are open on the firewall. Once connected, you can see from the monitoring section of RD Gateway manager, we are now connected to our remote resources through the Gateway on TCP 443 / UDP3391. Expand the site tree and locate the site which we generated the certificate for. The ID column shows the index of your site, subtract one from it. If you use RDS Gateway or RDS Web Access to connect external users to the corporate network, you can use the trusted SSL certificate from Let’s Encrypt instead of the self-signed certificate. After that, future RDP connections will connect with no messages. To redirect all incoming HTTP traffic to the HTTPS website URL, install the Microsoft URL Rewrite Module (, and make sure that the option Require SSL is disabled in the site settings. Once completed the certificate will appear in the Web Hosting section of the local computer certificates. This is beyond the scope of this guide as that procedure varies depending on your provider. Consider how to correctly install the Let’s Encrypt certificate to secure Remote Desktop Services on Windows Server. Let’s Encrypt will issue you a new certificate and bind it to the IIS website, and the automatic certificate renewal task will appear in the Task Scheduler. You will have to look in the documentation for Posh-ACME. We have confirmed that our HTTP validation is going to be successful. Ryan is an end-user computing specialist with a great passion for virtualization. This will be a series of two byte characters that are separated by spaces. You can create both using a wizard in one sitting. It is a simple wizard that allows you to select one of the websites running on the IIS, automatically issue and bind an SSL certificate to it. find out more about deploying RD Gateway in detail here:, Ryan Mangan works as the CTO at Systech IT Solutions. But you can automatically renew the SSL certificate for your website using simple scheduling. Since you will have a new Let’s Encrypt certificate when it is set to renew, you will need to copy the new cert to the RDP cert location in the server’s certificate store - and then perform the export and the rest of the steps each time. In the Add Domains to certificate, enter the FQDN for the RD Gateway Server. Point to note, the certificate expires in two months however you can configure the automatic renewal of the certificate. In our example, there is no need to use a certificate with aliases (multiple SAN – Subject Alternative Name), so just select an item 1. Using Let’s Encrypt certificates with Windows Admin Center.

Schedule this to run every day or so.

Assuming you’ve a simple all in one Remote Desktop Server setup with the roles RD Gateway, RD Connection Broker and RD Web Access, you have to import the certificate into the IIS site and additionally configure it for the installed RD roles.

He is the owner and author of, where he posts articles about remote desktop services, VMware, Microsoft Azure, Parallels RAS, KEMP, and other products and technologies. You MUST choose to include the cert’s Private Key when exporting. Download the latest release of the WACS client from the GitHub (in my case, this is version v2.0.10 – the file name is I have recently been working on a project to build and deploy a Terminal Server for a client and configure an RD Gateway to allow for external contractors to use it. In summary, has anyone tried to automate this use case? Right click on the site and click on Bindings. There is the certutil.exe utility which will generate a CSR and create a key in the right store (you then fulfill the challenge and import the cert only), Windows IIS cannot make use of certs on file stores they have to be in the cert store, I am working my way through the powershell side also going to log a request with the boulder team to make PFX an option as being able to download a PFX file from letsencrypt will simplify things for windows users, in the mean time if openssl is on the system the openssl syntax can be scripted, but i would like to do as much as i can with windows native tools. Add an HTTP binding to the default website in IIS on your RDS server. You can find the Let’s Encrypt IIS certificate in the computer certificate store under Web Hosting -> Certificates. so tossing up how to create an IIS installer plugin at the moment, whether to use hooks or the plugin system. A TLS/SSL certificate of a website allows to protect user data transferred over the public network against man-in-the-middle (MITM) attacks and provide data integrity. Can you confirm that this would allow me to pass the DNS challenge, if properly configured? Suppose, you have an IIS website running on Windows Server 2016. I bookmarked this conversation so that I can try to accomplish the same on my own, later on when I’ll set this up. You should be able to see the SSL certificate which we generated select in the drop down SSL certificate menu. Assuming you’ve a simple all in one Remote Desktop Server setup with the roles RD Gateway, RD Connection Broker and RD Web Access, you have to import the certificate into the IIS site and additionally configure it for the installed RD roles.

This task runs the command: C:inetpubletsencryptwacs.exe --renew --baseuri "". How to generate a Certificate for Microsoft Remote Desktop Servers. A Deep Dive into MSIX App Attach - Windows Virtual Desktop, Testing CimFS (Composite File System) – Windows Virtual Desktop, Ebook – Quickstart Guide to Windows Virtual Desktop, Azure Files Sizing Calculator for Windows Virtual Desktop, Ryan Mangan and Steve Horne: EUC Today and Tomorrow – Podcast Episode 331 – DABSCCRADIO, A Deep Dive into MSIX App Attach – Windows Virtual Desktop, Windows Server licence – Free trial to test this out. So I have the following script, it is designed to run after letsencrypt-win-simple's auto-renewal.

Plus is not a situation where you enter the host and credentials on the fly and you can access securely, you’d need to have a signed .rdp file that expires whenever there’s a renew. Copyright 2020 © Diverse Services (WA) Pty Ltd. All Rights Reserved | ABN: 33 159 816 618. This application will automatically renew the certificate for us and update the IIS bindings however, it won’t install the certificate into our RDS server.

For this example, I have chosen to use HTTP validation. Well now there is an easy way to do this in Group Policy. Create a website or blog at, Click to share on Twitter (Opens in new window), Click to share on LinkedIn (Opens in new window), Quick & Simple Remote Access Solution using MS RD Gateway 12 / 16 / 19 versions – ready to use within the hour,, WVD Reverse Connect – The Fish Tank Analogy. In a nutshell the Remote Desktop Gateway role provides a RDP type of SSL VPN remote access service over TCP 443 and UDP 3391. You should see the IIS splash screen. If you are in need of setting up remote access for workers quickly, this may be the answer. you will also need to use powerhsell to install the certificate:, note: our internal domain is a internet based name so we can do DNS challenges etc. Microsoft Windows, Let’s Encrypt and Microsoft Remote Desktop Services, Automating the Renewal of Remote Desktop Certificates, 365 Days Until Windows 7 & Server 2008 R2 End-Of-Life. In Unix you could use tr -d ' ' to remove spaces from a string, without having to do it by hand in a text editor. Your browser may warn you of an invalid cert authority. In this case, a small application will be created on the IIS web server through which Let’s Encrypt servers will be able to perform domain validation.Note – During the TLS/HTTP validation, your site must be accessible from the Internet by its full DNS name over HTTP (80/TCP) and HTTPS (443/TCP) protocols.

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