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11. September 2012

Zimbra: Setting up a free (real) “commercial” SSL certificate

Filed under: Linux,Security,Server Administration — Tags: , , , , , — Christopher Kramer @ 20:40

I recently wrote about how to configure a new self-signed certificate for Zimbra.

Today I want to explain you how you can do even better and setup a real SSL certificate by Startcom which will make those annoying browser warning messages go away 😉 And the best: It is all for free, thanks to Startcom! It is also important to have a real SSL-certificate for use with most smartphones.

Please note that you have to respect Startcom’s certificate policy, which might require a non-free class 2 certificate for your commercial use. See the policy for details. Thanks to Thomas for this remark. With “commercial” certificate, I here mean a “real” CA-signed certificate, which Zimbra calls “commercial”, no matter whether used in a commercial context or not.

First, create a Certificate Request (CSR) in Zimbra. To do so, ssh into your server, login as root and issue a command like this:

/opt/zimbra/bin/zmcertmgr createcsr comm -new -keysize 2048 -digest sha256
-subject "/C=US/ST=CA/L=Sunnyvale/O=Yahoo/OU=Zimbra Collaboration Suite/"

This is one line. What is important here, is that you use the domain name for which the certificate should be issued at the end (instead of Startcom will ignore everything else anyway, so you can leave country, state, organization and so on as is or change it, doesn’t matter. What is also important is that you define a keysize of 2048 as Startcom won’t accept 1024 bit keys anymore. This parameter is not documented in the wiki yet, and seems to be available for newer versions of Zimbra only. With a little trick, it should also be also possible for older versions of zimbra such as 5 (but better update to the new version anyway…).

Next thing you do is register at startcom if you do not have an account yet. You’ll get an S/MIME certificate by Startcom for free which you need to login to their control panel. Your browser will generate the secret certificate and store it in its internal storage. I’d recommend you to backup this certificate – you will not be able to login into your startcom account if you loose it.

Then at startcom, you use the validation wizard to validate your domain. This will send a mail to postmaster/hostmaster/ (you can choose which one) with being your domain. So you need access to one of these mailboxes to prove that you own the domain.

Then use the certificate wizard at Startcom to create a new certificate. Skip the certificate creation step! Instead, past the CSR created by Zimbra ( /opt/zimbra/ssl/zimbra/commercial/commercial.csr ) into the webform. (Better always create private certificates yourself, never use certificate generators by somebody else, not even the CA.)

Once the certificate is created by Startcom (usually takes some minutes), install it as described in the zimbra wiki:

  1. Store the new (public) certificate you get from Startcom somewhere (e.g. /root/commercial.crt )
  2. Download the root CA certificate
    wget -O /root/ca.pem
  3. Download the intermediary certificate from startcom
    # If your certificate is class 1:
    wget -O /root/ca_intermediary.crt
    # If your certificate is class 2:
    wget -O /root/ca_intermediary.crt
  4. Combine them:
    cat /root/ca_intermediary.crt /root/ca.crt > /root/ca_chain.crt
  5. Verify your certificate:
    /opt/zimbra/bin/zmcertmgr verifycrt comm /opt/zimbra/ssl/zimbra/commercial/commercial.key /root/commercial.crt /root/ca_chain.crt
  6. Deploy your certificate:
    /opt/zimbra/bin/zmcertmgr deploycrt comm /root/commercial.crt /root/ca_chain.crt
  7. Check:
    /opt/zimbra/bin/zmcertmgr viewdeployedcrt
  8. Restart Zimbra
    su – zimbra
    zmcontrol stop
    zmcontrol start

I hope this post was useful so some of you. If you have problems with one of the steps, just ask in the comments.

Read here how to redirect http to https to enforce the use of https.


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9. September 2012

Zimbra: Creating a new self-signed SSL certificate

Filed under: Linux,Server Administration — Tags: , , , , , , , , , — Christopher Kramer @ 10:04

I recently had to recreate the SSL certificate of a Zimbra server and surprisingly it was not as easy as the documentation looked like, so I’d like to document how it is done and make comments on some difficulties that might come up.

So this is how it is done (on a Ubuntu Server running Zimbra Network edition 6.0.16 GA):

  1. SSH into the server, login as root
  2. Switch to the zimbra-user using
    su - zimbra
  3. Then run the following commands:
     sudo /opt/zimbra/bin/zmcertmgr createca -new
     sudo /opt/zimbra/bin/zmcertmgr deployca
     sudo /opt/zimbra/bin/zmcertmgr deploycrt self
  4. Restart Zimbra. To do so, as user zimbra, issue these commands (no sudo here):
    /opt/zimbra/bin/zmcontrol stop
    /opt/zimbra/bin/zmcontrol start

So the difficulties I had and some remarks:

  • sudo kept asking me for a password when I typed in
    sudo zmcertmgr createca -new

    Seems I am not the only one with this problem. The zmcertmgr command is white-listed in /etc/sudoers so you should normally not be asked for a password. Run the following command to edit /etc/sudoers (do not edit it in any other way!)


    So make sure in this file the following line is included:

    %zimbra ALL=NOPASSWD:/opt/zimbra/bin/zmcertmgr

    The % at the beginning seems to belong there. Note that the zimbra wiki has typo (zmvertmgr) in this line.
    But although I had this line in there, sudo kept asking me for the password. So what finally worked was invoking zmcertmgr with the complete path (as done above).
    Update: It seems I had a typo in here myself. Make sure it is “zmcertmgr”  and not “zmzertmgr” 😉
    Thanks to the comment by erolha!

  • In the Zimbra Release notes, the last command for updating the certificate is
    sudo zmcertmgr deploycrt self -new

    I got this error:

    Can't deploy cert for -new.  Unknown service.

    Without -new (and the complete path), it went through well.

  • No zimbra documentation I found mentions that a restart of zimbra is required, but without a restart, the old certificate was still used when opening the webmailer or the admin interface via https.


I hope I could help some of you that run into one of these problems.