Monthly Archives: June 2013

Part 2 — vCenter 5.1 U1 — Creating and installing SSL certs for SSO.

Installing Certificates with the VMware SSL Certificate Automation Tool

  1. From and administrative prompt run c:\vmwarecerttool\ssl-environment.bat.  This is important because it sets the variables that we edited early on.
    sslenvironment
  2. Next run c:\vmwarecerttool\ssl-updater.bat
    Step2
  3. At this point backup all VMware Databases (VCDB, RSA, and VCU).  Also take a VMware snapshot of the three VMware VMs.
  4. Select Option 1 and then Option 8.  Print out the Detailed Plan.
    Detailedplan
  5. Press 9 to go back to the main menu and then choose option 3, “Update Single Sign-on”.  Say a huge prayer and then press 1 to “Update the Single Sign-on SSL Certificate.  You will be prompted for the Single Sign-on master password.  Did you remember to write down your single sign-on master password?  You will need this many times during this install.
    Step1

    Hopefully it was successful…
    successfulmessage
  6. Switch to the vCenter Inventory Service Server.  From an administrative prompt run c:\vmwarecerttool\ssl-environment.bat and then c:\vmwarecerttool\ssl-updater.bat.  Select Option 4 “Update Inventory Service” and then option 1 “Update the Inventory Service Trust to Single Sign-On.
    Step3
  7. Select option 3, “Update the Inventory Service SSL Certificate”.  You will be prompted for the SSO admin password.
    Step4
  8. Login to the vCenter Server.  From an administrative prompt run c:\vmwarecerttool\ssl-environment.bat and then run c:\vmwarecerttool\ssl-updater.bat.  Choose option 5, “Update vCenter Server” and then option 1, “Update the vCenter Server Trust to Single Sign-On”.
    Step5
  9. Make sure that you created an administrator account within vCenter to use for this install.  This will be needed for the next step!
  10. Select option 2, “Update the vCenter Server SSL Certificate”.  You will need the passwords for your vcenter administrator, SSO admin, and the vCenter system database password.
    Step6
  11. Next, select option 3, “Update the vCenter Server Trust to the Inventory Service”.
    Step7
  12. Go back to the Inventory Service Server and choose option 2, “Update the Inventory Service Trust to vCenter Server”.
    Step8

  13. Switch again to the vCenter Server and select option 5 to get to the main menu, and then option 6, “Update vCenter Orchestrator (vCO)”.  Select option 1, “Update the vCenter Orchestrator Trust to Single Sign-On”.
    Step9
  14. Select option 2, “Update the vCenter Orchestrator Trust to Single Sign-On”.
    Step10
  15. Select option 3, “Update the vCenter Orchestrator (vCO) SSL Certificate”.
    Step11
  16. Select option 5 to go back to the main menu.  Select option 7, “Update vSphere Web Client and Log Browser”.  Now select option 1, “Update the Web Client Trust to Single Sign-On”.  You will be prompted for the SSO admin password.
    Step12
  17. Now choose option 2, “Update the Web Client Trust to Inventory Service”.
    Step13
  18. Continue with option 3, “Update the Web Client Trust to vCenter Server”.
    Step14
  19. Next choose option 4, “Update the Web Client SSL Certificate”.  You will be prompted for the SSO admin password.
    Step15
  20. Continue by selecting option 5, “Update the Log Browser Trust to Single Sign-On”.  This will ask you for the SSO admin password.
    Step16

The last item for the certification tool is to choose option 6, “Update the Log Browser SSL Certificate”.  This will ask you for the SSO admin password.

Updating VUM SSL Certificate

  1. Backup all the files in the directory below.  Copy the rui.key, rui.crt, and rui.pfx files from the c:\certs\vum directory to c:\Program Files (x86)\VMware\Infrastructure\Update Manager\SSL
  2. Stop the VMware vSphere Update Manager Service.
    Step18
  3. In the C:\Program Files (x86)\VMware\Infrastructure\Update Manager directory launch the VMwareUpdateManagerUtility.exe application.
  4. Login to the vCenter server using proper credentials.
    Step19
  5. Click on the SSL Certificate option on the left side then check the box on the right side and click Apply.
    Step21
  6. If all goes well you should see the window below.  Restart the service as directed.
    Step22Go Back to Part 1
    https://favoritevmguy.wordpress.com/2013/06/17/part-1-vcenter-5-1-u1-creating-and-installing-ssl-certs-for-sso/

 

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Part 1 — vCenter 5.1 U1 — Creating and installing SSL certs for SSO.

There is a lot of information out there for installing vCenter 5.1, but the information is lacking for getting SSL certs working properly.  I first want to thank Derek Seaman over at www.derekseaman.com for his posts regarding what to do.  I have tried to shorten this a little bit for my own recollection.  Here is what I did to get SSL certs working.

Preparation

  1. Make sure you have installed the SSO Server, Inventory Service Server, and vCenter Server.  I used three separate machines for my environment, but you can use just one if you wanted to.
  2. Download and install the Visual C++ 2008 Redistributables (x64) and Win64 OpenSSL v0.9y from http://slproweb.com/products/Win32OpenSSL.html on your SSO server.
    Create a c:\certs folder on the SSO server containing the following subfolders:
    certsfolders
  3. Download the SSL Certificate Automation Tool from https://my.vmware.com/group/vmware/get-download?downloadGroup=SSL-TOOL-10.  Unzip this to c:\vmwarecerttool folder.
  4. Following Derek Seaman’s blog post http://www.derekseaman.com/2012/09/create-vmware-windows-ca-certificate.html , create a VMware-SSL template on your CA server.
  5. You will need the following information during the install:

SSO Administrator

Username: admin@System-Domain

Password:

 vCenter Administrator

Username:

Password:

 Original Database Password

 

Creating Certificates

 1.  Edit the ssl-environment.bat file located in c:\vmwarecerttool and fill in the appropriate information:

set sso_cert_chain=c:\certs\sso\chain.pem
set sso_private_key=c:\certs\sso\rui.key
set sso_node_type=single
set sso_admin_is_behind_lb=no

set is_cert_chain=c:\certs\inventory\chain.pem
set is_private_key_new=c:\certs\inventory\rui.key

set vc_cert_chain=c:\certs\vCenter\chain.pem
set vc_private_key=c:\certs\vCenter\rui.key

set ngc_cert_chain=c:\certs\WebClient\chain.pem
set ngc_private_key=c:\certs\WebClient\rui.key

set logbrowser_cert_chain=c:\certs\LogBrowser\chain.pem
set logbrowser_private_key=c:\certs\LogBrowser\rui.key

set vco_cert_chain=c:\certs\Orchestrator\chain.pem
set vco_private_key=c:\certs\Orchestrator\rui.key

set vum_cert_chain=c:\certs\UpdateManager\chain.pem
set vum_private_key=c:\certs\UpdateManager\rui.key

set sso_admin_user=admin@system-domain
set vc_username=corp\vminstaller

2.  Next, create the following configuration files in their respective folders.  Make sure that you name the files correctly.  Do not include the .cfg filename in the .cfg file.  I have done this…J  Do not change the organizationalUnitName!  I have created an example of the Inventory.cfg.  I got these from http://www.derekseaman.com/2012/09/vmware-vcenter-51-installation-part-2.html .

EXAMPLE: Inventory.cfg
[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:VCINV1, DNS:VCINV1.DOMAIN.LOC

[ req_distinguished_name ]
countryName = US
stateOrProvinceName = Missouri
localityName = Saint Louis
0.organizationName = IT
organizationalUnitName = vCenterInventoryService
commonName = VCINV1.DOMAIN.LOC


Inventory.cfg
[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your Inventory Server), DNS:(FQDN of your Inventory Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName = vCenterInventoryService
commonName = (FQDN of your Inventory Server)

SSO.cfg
[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your SSO Server), DNS:(FQDN of your SSO Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName = vCenterSSO
commonName = (FQDN of your SSO Server)

vCenter.cfg

[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your vCenter Server), DNS:(FQDN of your vCenter Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName =vCenterServer
commonName = (FQDN of your vCenter Server)

WebClient.cfg

[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your vCenter Server), DNS:(FQDN of your vCenter Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName =vCenterWebClient
commonName = (FQDN of your vCenter Server)

VUM.cfg

[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your vCenter Server), DNS:(FQDN of your vCenter Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName =VMwareUpdateManager
commonName = (FQDN of your vCenter Server)

LogBrowser.cfg

[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your vCenter Server), DNS:(FQDN of your vCenter Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName =vCenterLogBrowser
commonName = (FQDN of your vCenter Server)

Orchestrator.cfg

[ req ]
default_bits = 2048
default_keyfile = rui.key
distinguished_name = req_distinguished_name
encrypt_key = no
prompt = no
string_mask = nombstr
req_extensions = v3_req

[ v3_req ]
basicConstraints = CA:FALSE
keyUsage = digitalSignature, keyEncipherment, dataEncipherment
extendedKeyUsage = serverAuth
subjectAltName = DNS:(Your vCenter Server), DNS:(FQDN of your vCenter Server)

[ req_distinguished_name ]
countryName = (Country Code)
stateOrProvinceName = (State)
localityName = (City)
0.organizationName = (Organization)
organizationalUnitName =VMwareOrchestrator
commonName = (FQDN of your vCenter Server)

3.  You should now have one configuration file in each of the certificate folders you created earlier.  Next, we need to pull down the root certificate.  I am using Microsoft CA, so that is the only example I can give.  Open a browser and go to https://yourcaserver/certsrv/.  Make sure you fill in your CA server.  Click on Download a CA certificate, certificate chain or CRL. Change the encoding method to Base 64 and click Download CA certificate chain. Change the file name to cachain.p7b.

4.  Double click on the downloaded certificate, then locate the certificate in the console. If you have more than one certificate in the console, skip to step 3 below. If you have just one certificate, right click on the certificate and select All Tasks -> Export. Select Base-64 encoded and save the certificate with a filename of Root64.cer in the root of the Certs directory.

Notice that I have a root CA and a Subordinate CA
CACHAIN

5.  If you have a root and intermediate CAs (two or more certs in the console), you have some extra work. Export each certificate from the console as Base-64 and save into different files (e.g. Root64-1.cer and Root64-2.cer). You MUST save your Root CA as Root64-1.cer and the intermediary CA as Root64-2.cer.
RootCert

6.  We also need a concatenated file of the CAs (Root64.cer), in reverse order. Reverse order means the root is at the bottom of the file, and the subordinate CA is at the top.  From an administrative command prompt in the c:\certs folder run:
copy Root64-2.cer+Root64-1.cer Root64.cer
Combineroot

7.  Create a batch file in c:\certs called create_csr.bat.  Paste the following into this file:

Set OpenSSL_BIN=c:\OpenSSL\bin\openssl.exe

Set Cert_Path=C:\Certs

CD /d %Cert_Path%\vcenter\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config vcenter.cfg

CD /d %Cert_Path%\Inventory\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config inventory.cfg

CD /d %Cert_Path%\SSO\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config SSO.cfg

CD /d %Cert_Path%\UpdateManager\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config VUM.cfg

CD /d %Cert_Path%\webclient\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config webclient.cfg

CD /d %Cert_Path%\LogBrowser\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config LogBrowser.cfg

CD /d %Cert_Path%\Orchestrator\

%OpenSSL_BIN% genrsa 2048 > rui.key

%OpenSSL_BIN% req -out rui.csr -key rui.key -new -config Orchestrator.cfg

8.  Open an administrative command prompt and then browse to c:\certs.  Run the create_csr.bat.  This will create two files in each of the cert folders.  If the files don’t create, check the configuration files that you created earlier.

Example: Inventory Folder
inventoryexample

9.  Now it is time to mint the certificates using these two files.  Under c:\certs create another batch file.  This time call the batch file vCenter5.1_CertRequest.bat.  Paste in the following and make sure that you change the Certificate Authority Name.  This batch file can be found here http://www.derekseaman.com/2012/09/vmware-vcenter-51-installation-part-2.html .

:: Script to request vCenter 5.1 SSL certificates from a Microsoft CA
:: Modify these variables for your paths and CA information
:: Place your root64-1.cer and root64-1.cer (if using an intermediate CA)
:: in the Cert_Path directory. OpenSSL config files must already exist.
:: Also creates the chain.pem files for the VMware Certificate automation tool
::
:: Written by Derek Seaman, derekseaman.com
::

:: Certificate Authority Template name
Set Cert_Template=VMware-SSL

:: Certificate Authority Name
Set CA_Name=D001DC01\Contoso-D001DC01-CA
:: Path to OpenSSL
set OPENSSL_CONF=c:\OpenSSL\bin\openssl.cfg
Set OpenSSL_BIN=c:\OpenSSL\bin\openssl.exe

:: Path to your vcenter services directory with the config files
Set Cert_Path=C:\certs

:: Do not change anything below here
Set Root_CA_Cert=%Cert_Path%\Root64-1.cer
Set Sub_CA_Cert=%Cert_Path%\Root64-2.cer
Set CA_Chain=%Cert_Path%\Root.cer

if exist %Sub_CA_Cert% (
copy /B  %Sub_CA_Cert% + %Root_CA_Cert% %CA_Chain%
Set CA_Cert_Chain=%CA_Chain%
) Else (
Set CA_Cert_Chain=%Cert_Path%\root64.cer
)

CD /d %Cert_Path%\vcenter
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config vcenter.cfg
certreq -submit -q -f -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx

copy /B rui.crt + %CA_Cert_Chain% chain.pem
CD /d %Cert_Path%\Inventory
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config inventory.cfg
certreq -submit -f -q -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx

copy /B rui.crt + %CA_Cert_Chain% chain.pem
CD /d %Cert_Path%\SSO
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config SSO.cfg
certreq -submit -f -q -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx
copy /B rui.crt + %CA_Cert_Chain% chain.pem

CD /d %Cert_Path%\UpdateManager
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config VUM.cfg
certreq -submit -f -q -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx

copy /B rui.crt + %CA_Cert_Chain% chain.pem
CD /d %Cert_Path%\webclient
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config webclient.cfg
certreq -submit -f -q -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx

copy /B rui.crt + %CA_Cert_Chain% chain.pem
CD /d %Cert_Path%\LogBrowser
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config LogBrowser.cfg
certreq -submit -f -q -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx
copy /B rui.crt + %CA_Cert_Chain% chain.pem

CD /d %Cert_Path%\Orchestrator
%OpenSSL_BIN%  genrsa 2048 > rui.key
%OpenSSL_BIN%  req -out rui.csr -key rui.key -new -config Orchestrator.cfg
certreq -submit -f -q -config “%CA_NAME%” -attrib “CertificateTemplate:%Cert_Template%” rui.csr rui.crt
%OpenSSL_BIN%  pkcs12 -export -in rui.crt -inkey rui.key -certfile %CA_Cert_Chain% -name rui -passout pass:testpassword -out rui.pfx
copy /B rui.crt + %CA_Cert_Chain% chain.pem

You should see a bunch of messages like this:
successfulmessage

All of the certs folders should now contain some new files:
certsnewfiles

10.  Copy the c:\certs and c:\vmwarecerttool folder from the SSO server to both the Inventory and vCenter Server.  Part 2 will fail if you forget to do this.

Continue on with part 2.  https://favoritevmguy.wordpress.com/2013/06/17/part-2-vcenter-5-1-u1-creating-and-installing-ssl-certs-for-sso