How to Install the vSphere vCenter Root Certificate

 Certificates, ESXi, vCenter vCSA, VMware  1 Response »
Dec 082023
 
vCenter-Root-CA-Missing

Today we’ll go over how to install the vSphere vCenter Root Certificate on your client system.

Certificates are designed to verify the identity of the systems, software, and/or resources we are accessing. If we aren’t able to verify and authenticate what we are accessing, how do we know that the resource we are sending information to, is really who they are?

Installing the vSphere vCenter Root Certificate on your client system, allows you to verify the identity of your VMware vCenter server, VMware ESXi hosts, and other resources, all while getting rid of those pesky certificate errors.

Certificate warning when connecting to vCenter vCSA
Certificate warning when connecting to vCenter vCSA

I see too many VMware vSphere administrators simply dismiss the certificate warnings, when instead they (and you) should be installing the Root CA on your system.

Why install the vCenter Server Root CA

Installing the vCenter Server’s Root CA, allows your computer to trust, verify, and validate any certificates issued by the vSphere Root Certification authority running on your vCenter appliance (vCSA). Essentially this translates to the following:

  • Your system will trust the Root CA and all certificates issued by the Root CA
    • This includes: VMware vCenter, vCSA VAMI, and ESXi hosts
  • When connecting to your vCenter server or ESXi hosts, you will not be presented with certificate issues
  • You will no longer have vCenter OVF Import and Datastore File Access Issues
    • This includes errors when deploying OVF templates
    • This includes errors when uploading files directly to a datastore
File Upload in vCenter to ESXi host operation failed

In addition to all of the above, you will start to take advantage of certificate based validation. Your system will verify and validate that when you connect to your vCenter or ESXi hosts, that you are indeed actually connecting to the intended system. When things are working, you won’t be prompted with a notification of certificate errors, whereas if something is wrong, you will be notifying of a possible security event.

How to install the vCenter Root CA

To install the vCenter Root CA on your system, perform the following:

  1. Navigate to your VMware vCenter “Getting Started” page.
    • This is the IP or FQDN of your vCenter server without the “ui” after the address. We only want to access the base domain.
    • Do not click on “Launch vSphere Client”.
  2. Right click on “Download trusted root CA certificates”, and click on save link as.
    Link to download vCenter trusted root CA Certificates
  3. Save this ZIP file to your computer, and extract the archive file
    • You must extract the ZIP file, do not open it by double-clicking on the ZIP file.
  4. Open and navigate through the extracted folders (certs/win in my case) and locate the certificates.
    VMware vCenter Root Certificates
  5. For each file that has the type of “Security Certificate”, right click on it and choose “Install Certificate”.
  6. Change “Store Location” to “Local Machine”
    • This makes your system trust the certificate, not just your user profile
  7. Choose “Place all certificates in the following store”, click Browse, and select “Trusted Root Certification Authorities”.
    Screenshot to Place in Trusted Root Certification Authorities
  8. Complete the wizard. If successful, you’ll see: “The import was successful.”.
  9. Repeat this for each file in that folder with the type of “Security Certificate”.

Alternatively, you can use a GPO with Active Directory or other workstation management techniques to deploy the Root CAs to multiple systems or all the systems in your domain.

Active Directory Certificate Services Discussion and Install Guide

 Certificates, Microsoft, Video Posts, Windows Server, Windows Server 2022  2 Responses »
Oct 112021
 
Windows Server 2022 Logo

Today we’re going to discuss and deploy Active Directory Certificate Services on a Windows Server 2022 Server. Additionally, we’ll also be generating a domain certificate request inside of IIS and then assign the resultant certificate to a WSUS Server.

This video will demonstrate and explain the process of deploying a Windows Server 2022 Certification Authority with AD CS.

Check it out and feel free to leave a comment! Scroll down below for more information and details on the guide.

Windows Server 2022: Active Directory Certificate Services Discussion and Installation Guide

Who’s this guide for

This guide is perfect for a seasoned IT professional or a beginner who is looking at getting experience with Windows Server 2022.

What’s included in the video

In this guide I will walk you through the following:

  • Discussion
    • SSL Certificates (Host verification)
    • Internal Root Certification Authorities (Root CAs)
    • Internal Root CA vs Public Trusted Root CAs
    • HTTPS Scanning (Web Filtering) and SSL Certificates
    • Intermediate Certificate Authorities
    • Why ADCS?
    • AD CS Certificate Templates
    • Encryption
    • Certificate Issuance
  • Demonstration
    • Server Manager Role Installation
    • MMC Snap-in for Certificates (Local Computer)
      • Root CAs
    • Install Active Directory Certificate Services (AD CS)
      • Add Server Role
      • Root CA Trust Discussion
      • AD CS Installation on Domain Controller Installation
      • AD CS Prerequisites
      • Web Enrollment Discussion
      • AD CS and IIS Discussion
    • Install Internet Information Services (IIS) as pre-requisite
    • Configure Active Directory Certificate Services (AD CS)
      • Credentials
      • Role Configuration
      • Enterprise CA vs Standalone CA
      • Root CA vs Subordinate CA
      • Private Key Creation and Cryptographic options
      • Root CA Naming
      • Validity Period
    • Certification Authority MMC Usage
    • Root CA Replication to Domain (“gpupdate /force” and restart)
    • AD CS Certificate Templates Overview
      • Certificate Templates MMC
      • Duplicate and Customize Web Server Certificate Template
      • Enable Auto-Enrollment for Certificate Template
    • Use IIS to request certificate from Active Directory Certification Authority
      • Create Domain Certificate
    • Enable SSL on WSUS Server using Active Directory Certificate Services Certificate
      • Bind new certificate to IIS Web Server
      • Update GPO to reflect SSL URL and port number
      • Run “iisreset” on elevated command prompt
    • Demonstration Summary

What’s required

To get started you’ll need:

  • 1 x Server (Virtual Machine or Physical Server)
  • Microsoft Windows Server 2022 Licensing
  • A running Windows Server 2022 Instance (OSE)
  • A network router and/or firewall

Hardware/Software used in this demonstration

  • VMware vSphere
  • HPE DL360p Gen8 Server
  • Microsoft Windows Server 2022
  • pfSense Firewall

DST Root CA X3 Certificate Expiration Problems and Fix

 Certificates, Security, Sophos, Sophos UTM  139 Responses »
Sep 302021
 
ISRG and Let's Encrypt

Today, the DST Root CA X3 certificate expired, leaving many devices on the internet having issues connecting to services and certificates that use this Root CA, including those using Let’s Encrypt certificates.

Some of these problematic devices include Samsung Galaxy phones, iPhones, VDI zero and thin clients, and even Sophos UTM firewalls.

In my environment, I noticed a number of issues when browsing to websites that use the free Let’s Encrypt certificates, as the Web Protection Web Filtering service on my Sophos UTM firewall would report the certificate has expired and not allow me access to the websites using it.

The Problem

Let’s Encrypt originally used the “DST Root CA X3” certificate to issue Let’s Encrypt certificates. However, as time has passed and the service has been used more, they now use “ISRG Root X1” and “ISRG Root X2” as Root CA’s and “Let’s Encrypt R3” as an intermediate certificate.

Older devices may be using the older Root CA which expired today (September 30th, 2021). Please see https://letsencrypt.org/docs/dst-root-ca-x3-expiration-september-2021/ for more information.

The Fix

To fix this issue, you need to add the 2 new Root CAs to your computer or device.

Root CA Certificates (PEM format):

Intermediate Certificate (PEM format):

You can download them by clicking the links above or go to https://letsencrypt.org/certificates/ for more information and to download if you don’t trust the above links.

After downloading and adding these Root CAs and the Intermediate CA to your computer or device, you should have the full certificate chain to validate the Let’s Encrypt certificates. You only need to add the two root certificates. The Let’s Encrypt certificates that are used on websites that you visit and that you might have deployed on your servers should now work without any issues.

If you’re still having issues, you can try deleting the “DST Root CA X3” certificate from your existing Root CAs. Also, you may need to close and reopen any software and/or browsers for it to work with the new certificate.

HTTPS Scanning/Filtering Firewall Fix (Sophos UTM as example)

If you have a firewall that scans HTTPs traffic, you’ll need to add the two root certificates above to the HTTPS Certification authority list.

As an example, to fix this on the Sophos UTM firewall, follow the instructions below:

  1. Download the 3 certificates above.
  2. Log on to your Sophos UTM
  3. Navigate to “Web Protection”, “Filtering Options”, and “HTTPS CAs” tab.
  4. Disable the old “Digital Signature Trust Co. DST Root CA X3” Certificate in the list.
  5. Using the “Upload local CA”, browse to and select 1 of the 3 certificates, then click upload.
  6. Repeat step 5 for each of the 3 certificates listed above.
  7. The issue has been fixed! You should now see all 3 certificates in the “Local verification CAs” list.

The steps should be similar for other firewalls that provide HTTPS Scanning and Filtering.