5.x Commercial Certificates Guide

Revision as of 22:37, 26 August 2008 by Notpeter (talk | contribs) (Admininstration Console>Certificates: Note about only one open CSR at a time.)

General Overview

Installing a commercial certificate in ZCS version 5.0.0_GA and above is a straightforward process. The following is an overview of the steps you will take to install a commercial certificate.

  1. Generate a CSR via the Administration Console>Certificates or via the zmcertmgr command line utility.
  2. Receive the signed certificate.
  3. Receive the chain_certificates (if applicable).
  4. Install the certificate.


Admininstration Console>Certificates

This is the preferred method for installing commercial certificates. You simply start the Wizard and upload all the cert files and restart the Zimbra Services.

At the moment (8/26/08), according to Zimbra support, the web interface only supports having "one csr/private key at a time. Generating a new csr overrides the existing one and generates a new private key. If you want to generate more than one csr:

- you simply generate the first one which is downloaded to
 /opt/zimbra/ssl/zimbra/commercial directory (commercial.csr and commercial.key)
- move both files aside
- generate the second csr which would download to the same location above"


If the Administration Console>Certificates Wizard is not doing the job, we then resort to the command line.

Note: This tool must be run as root.

It requires the following:

  • The private key must exist in /opt/zimbra/ssl/zimbra/commercial directory and must be named commercial.key with permission set to 740.
  • The server certificate and the chain cert files must exist in a temp directory. E.g. /root/certs
  • The server cert must be named commercial.crt.
  • The chain cert files must be concatenated into one file called commercial_ca.crt.
  • Verify that the cert and the key match using this command:
/opt/zimbra/bin/zmcertmgr verifycrt comm /path/to/privatekey /path/to/commercial.crt /path/to/commercial_ca.crt
  • From the temp directory, deploy the cert and restart the zimbra services.
(a) sudo zmcertmgr deploycrt comm /path/to/commercial.crt /path/to/commercial_ca.crt
(b) zmcontrol stop ; zmcontrol start

Certificate Upgrade Issues

If you are upgrading from 4.5x to 5.0.x and the cert failed to upgrade successfully, you need to re-install the cert. You will need these pieces:

  1. The private key. This can be extracted from the Tomcat keystore. Zimbra Support can help with this process if you send the Tomcat keystore.
  2. The server certificate
  3. The chain cert files

With these pieces in hand, we can use the zmcertmgr to install the certificate as explained in #Importing commercial certificates from other mail systems to Zimbra 5.x.

Check to make sure that only the jetty alias exists in the keystore.

keytool -list -keystore /opt/zimbra/mailboxd/etc/keystore -storepass  `zmlocalconfig -s -m nokey mailboxd_keystore_password`

Delete the tomcat alias, if exists, with the following command.

keytool -delete -alias tomcat -keystore /opt/zimbra/mailboxd/etc/keystore -storepass `zmlocalconfig -s -m nokey mailboxd_keystore_password`

Importing commercial certificates from other mail systems to Zimbra 5.x

The steps are the same as the ones under #/opt/zimbra/bin/zmcertmgr.

GoDaddy Certificate in 5.x

Assuming the following is correct:

  • This is a new certificate.
  • You generated the CSR via the Administration Console.
  • You sent the CSR to get it signed and you received the following files:
    • gd_cross_intermediate.crt
    • gd_intermediate.crt
    • <server_name>.crt
    • gd_bundle.crt
  • The /opt/zimbra/ssl/zimbra/commercial has two files:
    • commercial.key
    • commercial.crt

You can install the certificate by logging in to the Administration Console and uploading the following files.

  • RootCA
  • gd_cross_intermediate.crt
  • gd_intermediate.crt
  • <server_name>.crt

Once you have uploaded these files, restart Zimbra services.

Network Solutions Certificate

1. Rename the <server_name.crt> file to commercial.crt and place it in the /opt/zimbra/ssl/zimbra/commercial 2. chmod 700 commercial.crt 3. Concatenate the chain files into one file and call it commercial_ca.crt

cat AddTrustExternalCARoot.crt NetworkSolutions_CA.crt UTNAddTrustServer_CA.crt >> commercial_ca.crt

4. cp commercial_ca.crt /opt/zimbra/ssl/zimbra/commercial

chmod 700 commercial_ca.crt

5. Run a check against the cert files.

/opt/zimbra/bin/zmcertmgr verifycrt comm

6. At this point and if the output looks promising, go ahead and deploy the cert.

/opt/zimbra/bin/zmcertmgr deploycrt comm commercial.crt commercial_ca.crt

7. Restart the Zimbra services.

su - zimbra
zmcontrol stop
zmcontrol start

8. Verify that the Web interface is loading correctly with the new certificate.

Note: This assumes that you have the private key in /opt/zimbra/ssl/zimbra/commercial named as commercial.key with the correct permissions.

Thawte SSL Certificate (SSL123 format)

1. Generate the CSR from admin console and get it signed by Thawte in .pem format. Save the cert in /opt/zimbra/ssl/zimbra/commercial and rename it to commercial.crt . This directory should also contain commercial.key, which was generated at the time of CSR creation.

2. Download ThawteServerCA_b64.txt and save it at /opt/zimbra/ssl/zimbra/commercial

3. Run following commands as root:

cd /opt/zimbra/ssl/zimbra/commercial/
/opt/zimbra/bin/zmcertmgr verifycrt comm commercial.key commercial.crt ThawteServerCA_b64.txt

If output of above commands looks good, proceed to install the certificate.

/opt/zimbra/bin/zmcertmgr deploycrt comm commercial.crt ThawteServerCA_b64.txt

4. Restart the Zimbra services.

su - zimbra
zmcontrol stop
zmcontrol start

5. Verify that the Web interface is loading correctly with the new certificate.

Install Verisign Test Certificate on Zimbra Server

See Install Verisign Test Certificate on Zimbra Server


LDAP/Nginx won't start and asks for a password

That means Zimbra can't read the key or the cert of the LDAP/IMAP proxy service on startup.

Here is what you can do:

1. You want to check to make sure the private key is not encrypted.

2. Manually link the cert to the services OR simply redeploy the certificate to relink the cert to the services.

(a)cp /opt/zimbra/ssl/zimbra/commercial/commercial.key /opt/zimbra/conf/sldapd.key
(b)cp /opt/zimbra/ssl/zimbra/commercial/commercial.key /opt/zimbra/conf/slapd.crt
(c)cp /opt/zimbra/ssl/zimbra/commercial/commercial.key /opt/zimbra/conf/nginx.key
(d)cp /opt/zimbra/ssl/zimbra/commercial/commercial.crt /opt/zimbra/conf/ngix.crt

3. Restart the Zimbra services.

Failed to create jetty.pkcs12

If you are seeing the following error when you try to install the certificate via Administration Console>Certificates,

Your certificate was not installed due to the error : system failure: XXXXX ERROR: failed to create jetty.pkcs12 
Message: Your certificate was not installed due to the error : system failure: XXXXX ERROR: failed to create jetty.pkcs12 
Error code: ZaCertWizard.prototype.installCallback Method: AjxException.UNKNOWN_ERROR Details:system failure: XXXXX 
ERROR: failed to create jetty.pkcs12

Check the following:

1. Make sure the permissions of the /opt/zimbra/mailboxd/webapps/zimbraAdmin/tmp/ directory is set to 644 zimbra:zimbra.

2. Clear all the current aliases in the mailboxd keystore except for the jetty alias.

keytool -delete -alias tomcat -keystore /opt/zimbra/mailboxd/etc/keystore -storepass `zmlocalconfig -s -m nokey mailboxd_keystore_password`

3. If you are running ZCS version 5.0.5, comment out line #539 of the /opt/zimbra/bin/zmcertmgr utility before deploying the cert. This is bug 27581 [[1]].

4. Until 5.0.9, check that commercial.crt last char is a cr, bug 31034 [[2]].

Private key and certificate mismatch

If you are seeing this error as you deploy the certificate:

Your certificate was not installed due to the error : system failure: XXXXX ERROR: Unmatching certificate
(/opt/zimbra/mailboxd/webapps/zimbraAdmin/tmp/current.crt) and private key (/opt/zimbra/ssl/zimbra/commercial/commercial.key) 
pair. Error code: ZaCertWizard.prototype.installCallback...

You need to regenerate the CSR, which will create a new key, and submit it to the CA to get it signed. You simply start the certificate installation again.

Problem with Certificate can cause MTA Failure

See Problem with Certificate can cause MTA Failure

Unable to get issuer certificate

If you are getting this error as you deploy the certificate:

XXXXX ERROR: Invalid Certificate:....error 20 at 0 depth lookup:unable to get local issuer certificate
XXXXX ERROR: provided cert isn't valid. 

or this error,

this alternate error error 2 at 1 depth lookup

That means the certificate path or chain is broken and you are missing certificate files. In most cases the intermediate cert. For more info on certificate path verification, please take a look at this url http://www.herongyang.com/crypto/openssl_verify.html


  • Inspect your CSR
openssl req -in <server.csr> -noout -text
  • Inspect your certificate
openssl x509 -in <server.crt> -noout -text
  • Clear the passphrase of the private key
openssl rsa -in <server.key> -out <server.key.decr>
  • Get Jetty keystore password
zmlocalconfig -s -m nokey mailboxd_keystore_password
  • Create a CSR via the CLI
sudo /opt/zimbra/bin/zmcertmgr createcsr <self|comm> [-new] [subject] [-subjectAltNames "host1,host2"]
  • View deployed certificate via the command line
 sudo /opt/zimbra/bin/zmcertmgr viewdeployedcrt
  • Convert the cert format from DER to PEM
openssl x509 -in input.cer -inform DER -out output.cer -outform PEM
Verified Against: Zimbra Collaboration Suite 5.x Date Created: 1/16/2008
Article ID: https://wiki.zimbra.com/index.php?title=5.x_Commercial_Certificates_Guide Date Modified: 2008-08-26

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