Remote Desktop Services – RemoteApp Certificate Issue

I was recently involved in a Remote Desktop Services deployment for three hundred users. After configured Remote Desktop Services and publishing a RemoteApp, which had been digitally signed with a Go Daddy certificate and deployed via an MSI, I was prompted with a “Do you trust the publisher of this RemoteApp program” warning as shown in the below screenshot.

Remote Desktop Services Do you trust the publisher of this RemoteApp program 300x172 Remote Desktop Services   RemoteApp Certificate Issue

Obviously this was going to be an inconvenience for users, so to resolve this issue I performed the following actions.

1. Create a new Group Policy object via the Group Policy Management Console.

2. Edit the GPO and navigate to the following location, User Configuration\Policies\Administrative Templates\Windows Components\Remote Desktop Services\Remote Desktop Connection Client.

3. Within the Remote Desktop Connection Client folder double click the “Specify SHA1 thumbprints of certificates representing trusted .rdp publishers” group policy object and check the enabled radio button.

4. Now open the SSL certificate you are using for RemoteApp signing, click the Details tab and then scroll down the details pane until you see the “Thumbprint” item. Click the thumbprint entry and you should now see a large alphanumeric string, copy this string and paste the contents into the “Comma separated list of SHA1 trusted certificate thumbprints” box in the GPO we were editing in step 3.

5. Now that you have pasted the thumprint string into the GPO, remove all space and capitalise all lower case letters of the string. For example, if your thumprint looks like this, “95 1f 22 02 c3 6e a6 b0 64 0c db 8e b5 4a bb 98 0c bd ed af” once you have pasted it into the GPO, you need to modify it to read like this, “951F2202C36EA6B0640CBD8EB54ABB980CBDEDAF”.

6. Close down the GPO editor and then link the created GPO to a users organisational unit where the RemoteApp users reside. Log a RemoteApp user off and back on again and test the RemoteApp program, you should now hopefully see that the certificate warning is suppressed and the application loads straight away.

That’s it, your all done.

Microsoft Exchange 2010 – SSL Certificates

I recently installed my first third party certificate into an Microsoft Exchange 2010 environment. This process is almost identical to how it is performed in Exchange 2007, however the PowerShell commands differ very slightly. Microsoft Exchange 2010 does actually support certificate requests and installations directly through the Exchange Management Console, however I’m not much of a fan of this, it has a slightly clunky feeling to it much like the Small Business Server 2008 implementation of wizard driven certifcate requests and installations.

For this certificate installation I was using a Go Daddy UCC 5 Domain certificate, which is more than adequate for Exchange 2010. You may see Exchange certificates branded as UCC (Unified Communications) or SAN (Subject Alternative Name), these are essentially the same, just different vendors choose to brand them differently. As a rule of thumb, always go for at least a five domain Unified Communications certificate otherwise you will find yourself in a pickle when it comes to adding subject alternative names. The following section of this post details the steps required to generate your CSR and install your certificate into your Exchange 2010 environment.

1. The first step of this process is to generate the CSR that will be used to tell your SSL vendor all about your environment. To make life a little easier, DigiCert have created a web based tool that will compile the required CSR PowerShell command for you, which you can find here

Hopefully once you have filled out the required fields in the DigiCert tool, you should have something very similar to the below screenshot. Please pay attention to the Subject Alternative Names used and the order that they have been entered in.

DigiCert CSR 300x159 Microsoft Exchange 2010   SSL Certificates

Please note that where is your public domain name, and where contoso.local is your local domain name. would the public DNS A record that is pointed to your internet endpoint, for example the global IP address of your router or firewall.

2. Once you have filled out of the required fields, click the generate button and then copy the generated PowerShell command to your clipboard. Open the Exchange Management Shell (EMS) on your Exchange 2010 server and paste the copied PowerShell command into the EMS and press return. Once this has completed, navigate to the C:\ drive on your server and open the generated .csr file in notepad. The content of this notepad file is the information you need to submit to your SSL vendor when they request CSR information.

3. When your certificate has been generated, download it from your SSL vendors website onto the root of the Exchange 2010 servers C:\drive. Once this has been performed, we need to action a PowerShell command to both import the new certificate and append this certificate to all Exchange 2010 services.  The PowerShell command you need to run is the following:

Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content -Path c:\your_certificate.cer -Encoding byte -ReadCount 0)) | Enable-ExchangeCertificate -Services IIS,POP,IMAP,SMTP

In the above command, please edit the -Path attribute to read the file location of where you have stored your downloaded certificate.

4. To verify the certificate installation, browse to Outlook Web Access from an external source, so for example to and ensure that the correct certificate is being utilised by clicking the padlock icon in Internet Explorer or your preferred browser.