How to replace default VCSA 5.5 certificates with Microsoft CA signed certificates

DISCLAIMER: This is a very lenghty procedure and I’ve changed some steps from the original KB trying to make it shorter; if I made some mistakes please let me know.

I don’t do this all the time but today I had to replace SSL certificates on a vCenter Virtual Appliance and since I know this will happen more and more often I thought I should write a shorter procedure since VMware KB is very detailed and, yet again, very long. At least it’s not as long as the infamous 96 steps of version 5.1.

Before proceding it’s good practice to shutdown your vCSA and take a snapshot.

Go to http://vcenter_ip_address:5480 or http://fqdn:5480 and chack that the “Certificate regeneration enabled” setting in the Admin tab of the vCSA web interface is set to “No” or we will lose all our work at first reboot:


Also, since we are going to use a Microsoft CA for this tutorial, it would be a good idea to take a look at KB2062108 and complete those steps before proceeding.

Note: This procedure is specific for vCSA 5.5. If you have a previous version of vCSA please refer to KB2036744.

Download and install the latest build of OpenSSL 0.9.8 on a machine of your choice. For convenience I installed it on a Windows VM in “C:\OpenSSL”.

Create the following folders:


Open a text editor:

[ req ]
default_md = sha512
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req
input_password = testpassword
output_password = testpassword

[ v3_req ]
basicConstraints = CA:false
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth, clientAuth
subjectAltName = DNS:vcva55, IP:, IP:ServerIPv6Address, DNS:

[ req_distinguished_name ]
countryName = US
stateOrProvinceName = NY
localityName = New York
0.organizationName = VMware
organizationalUnitName = vCenterApplianceUniqueServer
commonName =

Change the following lines:

  • subjectAltName: insert here data about name and IP of your vCSA (you can omit IPv6 if you don’t use it)
  • commonName: this must be your vCSA FQDN
  • all section [req_distinguished_name]
  • leave organizationalUnitName as it is

Save the file as “C:\OpenSSL\Certs\openssl_generic.cfg”.

We need to generate one .cfg file for each service, changing the “organizationalUnitName” by opening the “openssl_generic.cfg” file we just created:

  • organizationalUnitName = VMware vCenter Service Certificate (save as “C:\OpenSSL\Certs\vCenterSSO\openssl_vpxd.cfg”)
  • organizationalUnitName = VMware Inventory Service Certificate (save as “C:\OpenSSL\Certs\vCenterSSO\openssl_inventoryservice.cfg”)
  • organizationalUnitName = VMware LogBrowser Service Certificate (save as “C:\OpenSSL\Certs\vCenterSSO\openssl_logbrowser.cfg”)
  • organizationalUnitName = VMware vSphere Autodeploy Service Certificate (save as “C:\OpenSSL\Certs\vCenterSSO\openssl_autodeploy.cfg”)

You should now have a .cfg file for each service in each folder with a different organizationalUnitName.

To generate the certificate requests, assuming you have the same path I have, you can use the following commands.

cd c:\OpenSSL\bin

openssl req -new -nodes -out c:\openssl\certs\vCenterSSO\rui_vpxd.csr -keyout c:\openssl\certs\vCenterSSO\rui_vpxd.key -config c:\openssl\certs\vCenterSSO\openssl_vpxd.cfg

openssl req -new -nodes -out c:\openssl\certs\InventoryService\rui_inventoryservice.csr -keyout c:\openssl\certs\InventoryService\rui_inventoryservice.key -config c:\openssl\certs\InventoryService\openssl_inventoryservice.cfg

openssl req -new -nodes -out c:\openssl\certs\LogBrowser\rui_logbrowser.csr -keyout c:\openssl\certs\LogBrowser\rui_logbrowser.key -config c:\openssl\certs\LogBrowser\openssl_logbrowser.cfg

openssl req -new -nodes -out c:\openssl\certs\AutoDeploy\rui_autodeploy.csr -keyout c:\openssl\certs\AutoDeploy\rui_autodeploy.key -config c:\openssl\certs\AutoDeploy\openssl_autodeploy.cfg

Now you should also have a .key file and a .csr file in each respective directory.

To generate certificates from the .csr file login your Microsoft CA web interface (by default it is http://servername/CertSrv/):

  1. Click the Request a certificate link.
  2. Click advanced certificate request.
  3. Click the Submit a certificate request by using a base-64-encoded CMC or PKCS #10 file, or submit a renewal request by using a base-64-encoded PKCS #7 file link.
  4. Open the certificate request (rui_service.csr, as generated above for each component) in a plain text editor and paste this text into the Saved Request box.
  5. Select the Certificate Template as VMware Certificate.
  6. Click Submit to submit the request.
  7. Click Base 64 encoded on the Certificate issued screen.
  8. Click the Download Certificate link.
  9. Save the certificate as rui_service.crt, in the appropriate C:\OpenSSL\Certs\<service>\ folder.  (for example rui_vpxd.crt)
  10. Repeat Steps 2 to 10 for each of the additional service.
  11. Navigate back to the home page of the certificate server and click Download a CA certificate, certificate chain or CRL.
  12. Click the Base 64 option.
  13. Click the Download CA Certificate chain link.
  14. Save the certificate chain as cachain.p7b in the c:\openssl\certs\ directory.

By default, Microsoft CA certificates are generated with the .cer format. Either use Save As or change it to .crt before continuing.

When complete, you have four certificates (rui_service.crt) for each of the services generated in their respective c:\openssl\certs\<services> folders and the cachain.p7b file in the c:\openssl\certs\ folder.

Copy the c:\openssl\certs folder on the root of the vCenter filesystem via SCP, rename it to “ssl”, SSH to the vCSA, then:

service vmware-stsd stop
service vmware-vpxd stop

Rename all files in the service folders so that the .key file is named “rui.key” and the .crt file is named “rui.crt”.

On the vCenter Appliance, move where the cachain.p7b file is, then convert it to cachain.pem:

openssl pkcs7 -print_certs -in cachain.p7b -out cachain.pem

Now open cachain.pem with a text editor and remove any text before the first “—–BEGIN CERTIFICATE—–” and after “—–END CERTIFICATE—–“.

Note: This assumes there are no intermediate certificates in the Certificate Authority.

Copy the cachain.pem file in every service folder.

cd <vcenterservicefolder>
cat rui.crt cachain.pem > chain.pem
/usr/sbin/vpxd_servicecfg certificate change chain.pem rui.key

If all goes well you should receive this:


Check KB2057248 if you get a different result.

service vmware-stsd start
cd /etc/vmware-sso/register-hooks.d
./02-inventoryservice --mode uninstall --ls-server https://<em></em>:7444/lookupservice/sdk

Create the chain.pem file for every service:

cat rui.crt cachain.pem > chain.pem


cd <inventoryservicefolder>
openssl pkcs12 -export -out rui.pfx -in chain.pem -inkey rui.key -name rui -passout pass:testpassword
cp rui.key /usr/lib/vmware-vpx/inventoryservice/ssl
cp rui.crt /usr/lib/vmware-vpx/inventoryservice/ssl
cp rui.pfx /usr/lib/vmware-vpx/inventoryservice/ssl
cd /usr/lib/vmware-vpx/inventoryservice/ssl/
chmod 400 rui.key rui.pfx
chmod 644 rui.crt
cd /etc/vmware-sso/register-hooks.d
./02-inventoryservice --mode install --ls-server https://<em></em>:7444/lookupservice/sdk --user <em>sso_administrator</em> --password <em>sso_administrator_password
</em>rm /var/vmware/vpxd/inventoryservice_registered
service vmware-inventoryservice stop
service vmware-vpxd stop
service vmware-inventoryservice start
service vmware-vpxd start

Note: As there is a plain-text password on the above command, to avoid the history file showing the contents of the password because it is in plain text in the command above, run the unset HISTFILE command prior to executing any step containing a password.

Note: The default SSO administrator username for vCenter Single Sign-On 5.5 is administrator@vSphere.local

cd /etc/vmware-sso/register-hooks.d
./09-vmware-logbrowser --mode uninstall --ls-server https://<em></em>:7444/lookupservice/sdk
cd <logbrowserservicefolder>
<code>openssl pkcs12 -export –out rui.pfx –in chain.pem -inkey rui.key –name rui –passout pass:testpassword</code>
cp rui.key /usr/lib/vmware-logbrowser/conf
cp rui.crt /usr/lib/vmware-logbrowser/conf
cp rui.pfx /usr/lib/vmware-logbrowser/conf
cd /usr/lib/vmware-logbrowser/conf
chmod 400 rui.key rui.pfx
chmod 644 rui.crt
cd /etc/vmware-sso/register-hooks.d
./09-vmware-logbrowser --mode install --ls-server https://<em></em>:7444/lookupservice/sdk --user <em>sso_administrator</em> --password <em>sso_administrator_password
service vmware-logbrowser stop
service vmware-logbrowser start

In this environment the AutoDeploy service is not started so I’m skipping this step. (refer to KB2057223 to complete this step)

You can now restart the vCenter Server Appliance and chek that the certificates have been successfully replaced.


Related documents
Configuring Certificate Authority (CA) signed certificates for vCenter Server Appliance 5.5 (2057223)
Creating a Microsoft Certificate Authority Template for SSL certificate creation in vSphere 5.x (2062108)
Decoding a non-zero VC_CFG_RESULT for failed vpxd_servicecfg certificate changes (2057248)
Configuring certificates signed by a Certificate Authority (CA) for vCenter Server Appliance 5.1 (2036744)

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