Generate CSR with SAN from Windows Server and Submit to MS CA to Sign for IIS and RDP Services

While working in CyberArk PAS solution, there are many times the servers are required to get CA signed certificates to reduce certificate warning. Here are two typical cases for CyberArk deployment:
1. PSM RDS Services
2. PVWA IIS Server

Those steps are more Windows System Administrator tasks, not specifically for CyberArk.

CA Root Certificate

For domain joined machine, it has automatically installed CA Root Certification, which you will find it from Trusted Root Certification Authorities folder

For non-domain joined machine, to get domain CA root certificate, you will need to use CA web service to download CA root certificate and install it on local machine.

Microsoft CA service web url:

from any domain joined server: http://dc1.51sectest.dev/certsrv
from your CA server: http://localhost/certsrv

PSM and PVWA will require a CA signed certificate for security reasons. To get a CA signed certificate for your RDS and IIS PVWA application, you will need to generate CSR from those servers, then send it to CA to sign for a new CA-signed web certificate.

PSM RDS Service Certificate

By default, PSM RDS is using a self signed certificate. When end user RDP connecting to PSM, following certificate warning will pop up. The end users will need install this self-signed certificate into their local certificate storage, the connect sessions can continue.

A better solution is to let RDS service to use a CA signed certificate. Since in domain environment, all end user machines have installed CA root certificate, it will trust this RDS certificate so this kind of warning message can be avoided.

Note: Self-signed certificate is generated by RDS service. It will be placed in the remote desktop certificate store location. Even you deleted this self-signed certificate, it will be re-generated after a reboot.

YouTube Video:

Note: Chrome requires SSL Certificates to list the site name(s) in the subject alternative name (SAN) to be trusted. Usage of common name only is not seen as secure enough, and will result in a certificate validation error in Chrome.

Here is the steps to generate a CSR , send to CA to sign, import CA signed certificate to server , then assign it to RDS service.

1 Generate CSR from MMC Certificate Snap-in

Commands:

Certmgr.msc
certlm.msc

You can run MMC then add Certificate Snap-in. Go to personal -> certificate , right click your mouse at right panel space, choose All Tasks -> Advanced Operations -> Create Custom Request ...

Or directly Request New Certificate:

You can either do following bulletins or just click three times next :

Click next in Certificate Enrollment Wizard’s welcome window
Select “Proceed without enrollment policy” under Custom Request & click next
In Custom Request window Select (No template) Legacy key & PKCS #10 as request format
And Click Next

You will get following page, un-collapse detail , then click properties :

Adding following properties, especially alternative name:

Choose Server Authentication as Extended Key Usage:

Make private key exportable

Save CSR into local folder:

2 Submit your CSR file to CA to sign:

Go to your local MS CA page , request a new certificate - > submit an advanced certificate request

Choose Base 64 encoded format for your downloaded certificate:

3 Install your signed CA certificate into PSM server
Double click downloaded CA signed certificate from PSM server.

Click Install Certificate... button to import it into your local certificate storage. Choose local machine for store location.
Choose Personal for your certificate store:

4 Export your imported certificate to PCKS format

Right click your certificate and choose export...

Make sure export private key:

Put in a password so you can continue next step:

Give a proper name and save it to local with extension name .pfx.

5 Import it into RDS
Open Server manager - > Remote Desktop Services -> Overview - > Deployment Overview -> Tasks -> Edit Deployment Properties

Certificates -> select existing certificate...

Choose the exported certificate from previous step, and enter the password:

Click OK to complete all configuration. Now your RDS service has a CA signed certificate.

There are two RDS services which will need to assign this certificate.

PVWA IIS Server Certificate

By default installation, when end user connect to your https://<PVWA site.51sectest.dev>/PasswordVault will result in the certificate error, NET::ERR_CERT_COMMON_NAME_INVALID. This is to be expected due to the self-signed certificate created during the PVWA prerequisite script. One solution is by select browser page's notification , Advanced > Proceed to https://<PVWA site.51sectest.dev>/PasswordVault (unsafe)

Another better solution is to install CA signed certificate for your PVWA IIS service. Similar steps as RDS certificate process.

After you got signed CA signed certificate and imported into PVWA server local certificate personal location, launch IIS manager from Server manager -> IIS:

Assign the new imported certificate to https (443) service on Default Web Sites.

YouTube video for CyberArk System:

Generate CSR from IIS manager - Not Working for PVWA

IIS manager does has a way to generate CSR for your website. But it will not always work for our configuration. Strongly suggest no need to try this, since it does not allow us to add SAN (Subject alternative name).

You will not be able to generate appropriate certificate from IIS manager using following method since it will not be able to get you to customize "Subject Alternative name", which will include your PVWA's FQDN name and load balancer's FQDN name such as PVWA1.51sectest.corp, and PAM.51sectest.corp.

Here is this different way to use IIS manager to generate CSR, which will not work if you have multiple subject name such as in load balance use case.

Start IIS Manager. One quick way to do this is by opening the Run command, then typing inetmgr and clicking the OK button.

Select the server in the Connections pane, on the left side of the window. Double-click the Server Certificates icon, located under IIS in the center pane of the window.
Click the Create Certificate Request… link, in the Actions pane on the right side of the window.

All those steps look fine, but the cert won't work with our PVWA website since the certificate is missing SAN field information. We will have to use our CertLM.msc to generate proper CSR and submit CA to sign for it.