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VMware vSphere vCenter replace machine SSL certificate with custom CA signed certificates

There is a best security practice to implement authorized SSL Certificates on VMware infrastructure. Here I am installing certificates on the vSphere vCenter server. By default VMCA (VMware Certificate Authority) signed certificate is installed on the vCenter server. Which you can see under vSphere Client >> Administration >> Machine SSL Certificate >> View details or you can check the same on the browser Not secure option it will show Certificate is not valid and you can see it is issued by VMware CA by clicking it.

Microsoft Active directory certificate service adcs ssl openssl vsphere client browser certficate not valid not secure viewer cert common name organization validity fingerpint cookie vcenter vmca vsphere vmware esxi.jpg

To replace the default VMCA assigned certificate Go to settings (3 bar button left top side) in vSphere Client, choose Administration from list. Navigate and expand to Certificates and go to Certificate Management. In the Machine SSL Certificate (__MACHINE_CERT box) click ACTIONS link and select Generate Certificate Signing Request (CSR).

Microsoft certificate services ms adcs vmware vsphere vcenter esxi vsphere client administration certificate management machine ssl certificate vmware certificate authority vmca sts trusted root private key.jpg

It opens Generate CSR Wizard. Here enter information for a new SSL certificate. Info you need to provide is Common name (vCenter FQDN), Organization Unit, Country, State/Province, Locality, Email Address, Host (vCenter FQDN), Subject Alternative Name (Optional) (SANs), Private Key size. Click Next.

It will generate CSR as can be seen inside the box, Copy or download this CSR (Certificate signing request) as shown below, I will use and provide the content of this CSR in my Certificate Authority to be signed in the next task.

Microsoft CS vmware vsphere machine certificate vcenter generate csr certificate service request form common name organization unit state country host san key adcs .jpg

I am on my in-house Certificate Authority (Microsoft Active Directory Certificate Services) certsrv portal in the browser. Use this Web site to request a certificate for your Web browser, Email client, or other program. By using a certificate, you can verify your identity to people you communicate with over the Web, sign and encrypt messages, and depending upon the type of certificate you request, perform other security tasks.

Check this important article: Install and configure certificate authority (CA) on Microsoft Windows server with Group Policy

You can also use this Web site to download a certificate authority (CA) certificate, certificate chain, or certificate revocation list (CRL), or to view the status of a pending request.

Select a task by clicking Request a certificate. Submit an Advanced certificate request

Microsoft active directory certificate services crl revocation list chain vmware vsphere vcenter esxi trusted root certificate management pending request generate CSR certificate service request STS vmca.jpg

To submit a Certificate request or Renewal Request or saved request to CA, paste a base-64-encoded CMC or PKCS #10 certificate request or PKCS #7 renewal request generated by an external source (such as a Web server) in the Saved request box.

Here In the saved request the either use the CSR content copied or downloaded file from vCenter Server certificate management (Block from Begin to End). Change Certificate Template to Web Server.

Microsoft Active Directory Certificate Services submit certificate request or renewal request cmc pkcs base-64 der template vmware vsphere vCenter esxi vmca machine ssl certificate attribute thumbprint.jpg

Select Base 64 encoded option and click Download Certificate for issued requested certificate.

Microsoft certificate issued MS active directory certificate services adcs der encoded base 64 encoded download certificate chain ssl openssl cer pem crt certsrv vmware vsphere vcenter esxi vcsa mangement.jpg

Next go back to the Welcome page of certsrv CA web portal. Click Download a CA certificate, certificate chain or CRL. This Root CA certificate will be required in the next step.

MIcrosoft Active Directory Certificate services Authority ca certifficate root web enrollment.jpg adcs certificate authority vmca vmware vsphere vCenter pfx vcsa esxi subordinate.jpg

Click Download CA certificate and rename it to root.cer. I am keeping all certificate files in one directory. This Root CA certificate will be required in the next step.

Microsoft Active Directory Certificate services der base 64 ssl install ca certificate download ca certification chain latest base crl csr vmware vsphere vcenter esxi management certificate.jpg

Go back to vCenter Server >> Administrations >> Certificate management. Click on the Machine SSL Certificate >> ACTIONS button and choose Import and Replace Certificate.

VMware vSphere vCenter ESXi virtualization security best practices certificate management machine ssl certicicate __machine_cert private key chain import and replace certiicate certificate singing request csr generate vmca.jpg

In the Replace vCenter Server Certificate Wizard, choose option Replace with external CA certificate where CSR is generated from vCenter Server (private key embedded) and click Next.

Note: vCenter Server services will be automatically restarted after successful replacement of the machine SSL certificate. So plan for proper vCenter server service's restart downtime.

VMware vSphere vCenter ESXi replace vcenter server certificate vmca external CA certificate where CSR generated private key embedded external CA requires private key.jpg

In the next page of Replace with externally signed certificate and private key under Machine SSL certificate BROWSE File and select certnew.cer file and in the Chain of trusted root certificates, select root.cer after clicking BROWSE File button. Click REPLACE button.

vmware vsphere vCenter esxi replace certificate externally signed certificate private key import chain of trusted root certificates machine ssl certicate adcs certificate authority services

Once you click REPLACE button you will see behind there is a Success message as certificate replaced on vCenter server machine. Connection will Timed out and your vSphere Client session will no longer be authenticated. In the background vCenter Server services are being restarted, so it will take some time to come those services up and vCenter server get working.

Vmware vsphere vCenter esxi vcsa connection timeout vsphere client machine ssl certificate __machine_cert sts singing certificate vmware certificate authority vmca trusted root certificates adcs services.jpg

After few minutes refresh vCenter Server url in the browser, As you can see padlock sign with Connection is secure and the certificate issued successfully replaced by in-house Certificate Authority.

VMware vSphere vCenter esxi certificate authority ssl certificate brwser connection is secure missing common name cn organization unit validity period fingerprint thumbprint sha256 certificate viewer.jpg

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