Ajcody-Notes-SSLCerts

- This article is NOT official Zimbra documentation. It is a user contribution and may include unsupported customizations, references, suggestions, or information.

SSL Certificate Issues

Actual SSL Certificate Issues Homepage

Please see Ajcody-Notes-SSLCerts

Resources For SSL Certificates

General
Trouble Shooting
- Cannot_install_a_Commercial_Certificate_in_Zimbra_5.0
- Private_key_and_certificate_mismatch
- Recreate Self-Signed SSL Certs
  - I believe this wiki page has the best instructions. Sorry for the confusion about the state of the wiki pages on ssl certs. We are attempting to get them cleaned up.
    - Problem_with_Certificate_can_cause_MTA_Failure#For_Multi-Server:_Run_this_on_all_other_systems_in_the_multi-server_setup
  - Zmcertinstall#Single-Node_Self-Signed_Certificate
    - Has "Multi-Node Self-Signed Certificate" instructions as well.
  - Recreating_a_Self-Signed_SSL_Certificate
- 4.5.x_to_5.0.x_Certificate_Upgrade_Issues
- Failed_to_create_jetty.pkcs12
- LDAP/Nginx_won't_start_and_asks_for_a_password
- Problem_with_Certificate_can_cause_MTA_Failure
- Unable_to_get_issuer_certificate
Specific Cert Wiki Pages:

Bug & RFE's Related To SSL

"multiple SSL certificates on one server"
- http://bugzilla.zimbra.com/show_bug.cgi?id=8128
  - Allot of private comment details unfortunately.

Ldap Doesn't Start After Cert Changes Or Upgrade

Example of error:

[zimbra@server-01 ~]$ zmcontrol start
Host server-01.DOMAIN.com
        Starting ldap...Done.
FAILED
Failed to start slapd.  Attempting debug start to determine error.
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:0906D06C:PEM routines:PEM_read_bio:no start line pem_lib.c:647
TLS: error:02001002:system library:fopen:No such file or directory bss_file.c:352
TLS: error:20074002:BIO routines:FILE_CTRL:system lib bss_file.c:354
main: TLS init def ctx failed: -1

The fix is described in:

http://www.zimbra.com/forums/administrators/23104-5-0-10-upgrade-problem.html

More details as shared by a customer:

I moved the "ca" directory to "ca.BAK" to back it up, made a new ca directory, and then went through the steps detailed in that post.  Once done, zimbra started up without a problem:

1) Clear all the contents of the /opt/zimbra/conf/ca directory by backing them up
somewhere on disk.
2) Copy the /opt/zimbra/ssl/zimbra/commercial/commercial.key /opt/zimbra/conf/ca/ca.key
3) Copy /opt/zimbra/ssl/zimbra/commercial/commercial.crt /opt/zimbra/conf/ca/ca.pem
4) Create the hash value
ln -f -s ca.pem /opt/zimbra/conf/ca/`openssl x509 -hash -noout -in
/opt/zimbra/conf/ca/ca.pem`.0
5) Chmod 644 /opt/zimbra/conf/ca/*
6) Restart the zmcontrol


A sample of what the /opt/zimbra/conf/ca directory looked like:

lrwxrwxrwx  1 root root   20 Apr  9 20:29 0bb21872.0 -> commercial_ca_26.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 0c364b2d.0 -> commercial_ca_14.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 0e82f83a.0 -> commercial_ca_36.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 11f154d6.0 -> commercial_ca_49.pem
lrwxrwxrwx  1 root root   19 Apr  9 20:29 128b9c8d.0 -> commercial_ca_9.pem
lrwxrwxrwx  1 root root   19 Apr  9 20:29 1a147d5b.0 -> commercial_ca_5.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 1bb6c7e0.0 -> commercial_ca_24.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 1c647a6d.0 -> commercial_ca_21.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 256fd83b.0 -> commercial_ca_33.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 25f0cbee.0 -> commercial_ca_23.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 2d047263.0 -> commercial_ca_28.pem

There we many more of the above entries, all of which pointed to .pem files that didn't exist.

There was also:
lrwxrwxrwx  1 root root    6 Apr 13 11:43 555ebb99.0 -> ca.pem
lrwxrwxrwx  1 root root   17 Apr  9 20:29 8e6e2991.0 -> commercial_ca.pem
lrwxrwxrwx  1 root root   17 Apr 13 11:43 c33a80d4.0 -> commercial_ca.pem
lrwxrwxrwx  1 root root   20 Apr  9 20:29 c527e4ab.0 -> commercial_ca_57.pem
-rw-r--r--  1 root root  887 Apr 13 11:43 ca.key
-rw-r--r--  1 root root  989 Apr 13 11:43 ca.pem
-rw-r--r--  1 root root 1155 Apr 13 11:43 commercial_ca_1.pem
-rw-r--r--  1 root root 1156 Apr 13 11:43 commercial_ca.pem

zmcertmgr output:

./zmcertmgr deploycrt comm /opt/zimbra/certs/server-01.DOMAIN.com.crt /opt/zimbra/certs/ca_chain-server-01.DOMAIN.com.crt
** Verifying /opt/zimbra/certs/server-01.DOMAIN.com.crt against /opt/zimbra/ssl/zimbra/commercial/commercial.key
Certificate (/opt/zimbra/certs/server-01.DOMAIN.com.crt) and private key (/opt/zimbra/ssl/zimbra/commercial/commercial.key) match.
Valid Certificate: /opt/zimbra/certs/server-01.DOMAIN.com.crt: OK
** Copying /opt/zimbra/certs/server-01.DOMAIN.com.crt to /opt/zimbra/ssl/zimbra/commercial/commercial.crt
** Appending ca chain /opt/zimbra/certs/ca_chain-server-01.DOMAIN.com.crt to /opt/zimbra/ssl/zimbra/commercial/commercial.crt
** Saving server config key zimbraSSLCertificate...done.
** Saving server config key zimbraSSLPrivateKey...done.
** Installing mta certificate and key...done.
** Installing slapd certificate and key...done.
** Installing proxy certificate and key...done.
** Creating pkcs12 file /opt/zimbra/ssl/zimbra/jetty.pkcs12...done.
** Creating keystore file /opt/zimbra/mailboxd/etc/keystore...done.
** Installing CA to /opt/zimbra/conf/ca...done.

===Moving Your Certificates To New Or Another Server===

Please see [[Transfer_SSL_certificates_between_servers]]

===Commercial Cert Error - Subject Does Not Start With / ===

As reported by a customer to me:

''When creating a commercial cert for a server the zmcertmgr will fail if you don't supply a subjectAltName ----  Took me awhile to figure this out since the error isn't correctly describing the problem.  It says that "Subject does not start with '/'."  Which is incorrect.  Subject does start with "/" , it's the subjectAltName that was needed.  After I supplied this name, it generated the csr.  Here are my commands for your own reference.''

: I modified the Some* entries below.

 /opt/zimbra/bin/zmcertmgr createcsr comm -new -subject "/C=US/ST=SomeState/L=SomeCity/O=Some Community College/OU=ITS/CN=zimbra.somecommunitycollege.edu" -subjectAltNames zimbra.somecommunitycollege.edu

''then I went to thawte and applied for a ssl cert.''

===How To Setup Certs With CACert.org - Free Certs===

====CaCert.Org References====

Free Certs with http://www.cacert.org/ 

====How-To (tested on 5.0.2)====

Note, the following :

 su - root ; cd /opt/zimbra/ssl/zimbra/commercial/

included in all steps in case someone is skipping through instructions.

=====Clean up and start fresh=====

 su - root
 cd /opt/zimbra/ssl/zimbra/commercial/
 tar -czvf /tmp/ssl.commercial.backup.tar.gz *
 rm -rf *

=====Generate new csr=====

 [ su - root ; cd /opt/zimbra/ssl/zimbra/commercial/ ]
 /opt/zimbra/bin/zmcertmgr createcsr comm -new

This uses the defaults, note the items to change.

 /opt/zimbra/bin/zmcertmgr createcsr comm -new "/C=US/ST=TX/L=Somewhere/O=Company, Inc./OU=ITDepartment/CN=mail.CHANGEME.com"

=====Confirm=====

 [ su - root ; cd /opt/zimbra/ssl/zimbra/commercial/ ]
 ls -la

There should only be two files and time/date should match - commercial.csr & commercial.key

 cat /opt/zimbra/ssl/zimbra/commercial/commercial.csr
  -----BEGIN CERTIFICATE REQUEST-----
 [delete]CCAWwCAQAwgZkxCzAJBgNVBAYTAlVTMQwwCgYDVQQIEwNOL0ExDDAKBgNV
 [delete]4vQTEjMCEGA1UEChMaWmltYnJhIENvbGxhYm9yYXRpb24gU3VpdGUxIzAh
 [delete]AsTGlppbWJyYSBDb2xsYWJvcmF0aW9uIFN1aXRlMSQwIgYDVQQDExttYWls
 [delete]nRlcm5hbC5ob21ldW5peC5jb20wgZ8wDQYJKoZIhvcNAQEBBQADgY0AMIGJ
 [delete]AOri9/m6RtM1vASBROPgLvkUYybwf2WDI2xTdKUuAMI0rTpMH1IzjPRP/J+m
 [delete]RQTiJe1mRX3rJCy3qVooVzsLe2yJ1+rs3FzLSfQhazK6PqMD8GhpqHO0Y75
 [delete]LEA/qdOCrTFjosO9C3j3WPCW8lutTxf/QsoKGkIVs5tjAgMBAAGgKTAnBgkq
 [delete]0BCQ4xGjAYMAkGA1UdEwQCMAAwCwYDVR0PBAQDAgXgMA0GCSqGSIb3DQEB
 [delete]A4GBAKMLVFilRjI9xvU/vZmP69yReVZyxa5YVpF/cEvwFwbOU6E4USkdONGT
 [delete]DRj1XxfzYD+CDf8TVuTY4tapaLvKPRUtdd/mM1PidY5t126QAObyKjHBRzy
 [delete]RJFQeP+0ktxcYJ99+sfiescwR/qzPJM58i6daqmMamQBZi
   -----END CERTIFICATE REQUEST-----

=====Sign up for cacert.org use=====

Goto http://www.cacert.org/

Sign up - https://www.cacert.org/index.php?id=1

Verify the email the confirmation email.

Add a domain , it will send an email to some "admin" account to the domain. Make sure you can get it before you do this.

=====Get New Server Certificate=====

Now do a New Server Certificate from your administration page at http://www.cacert.org/

You'll copy in the /opt/zimbra/ssl/zimbra/commercial/commercial.csr contents in window [all of it].

It'll generate your cert. on the webpage.

Copy this onto the server [paste in cert details]:

 vi /opt/zimbra/ssl/zimbra/commercial/commercial.crt
 -----BEGIN CERTIFICATE-----
 [delete]TCCAl2gAwIBAgIDBPRRMA0GCSqGSIb3DQEBBQUAMHkxEDAOBgNVBAoTB1Jv
 [delete]0ExHjAcBgNVBAsTFWh0dHA6Ly93d3cuY2FjZXJ0Lm9yZzEiMCAGA1UEAxMZ
 [delete]2VydCBTaWduaW5nIEF1dGhvcml0eTEhMB8GCSqGSIb3DQEJARYSc3VwcG9y
 [delete]NlcnQub3JnMB4XDTA4MDQxMTIwMjQzNloXDTA4MTAwODIwMjQzNlowJjEk
 [delete]1UEAxMbbWFpbDMuaW50ZXJuYWwuaG9tZXVuaXguY29tMIGfMA0GCSqGSIb3
 [delete]AQUAA4GNADCBiQKBgQDq4vf5ukbTNbwEgUTj4C75FGMm8H9lgyNsU3SlLgDC
 [delete]B9SM4z0T/yfpoZc3yUUE4iXtZkV96yQst6laKFc7C3tsidfq7Nxcy0n0IWs
 [delete]BoaahztGO+ZgsfCxAP6nTgq0xY6LDvQt491jwlvJbrU8X/0LKChpCFbOb
 [delete]QABo4HcMIHZMAwGA1UdEwEB/wQCMAAwNAYDVR0lBC0wKwYIKwYBBQUHAwIG
 [delete]QUFBwMBBglghkgBhvhCBAEGCisGAQQBgjcKAwMwCwYDVR0PBAQDAgWgMDMG
 [delete]QUFBwEBBCcwJTAjBggrBgEFBQcwAYYXaHR0cDovL29jc3AuY2FjZXJ0Lm9y
 [delete]QYDVR0RBEowSIIbbWFpbDMuaW50ZXJuYWwuaG9tZXVuaXguY29toCkGCCsG
 [delete]wgFoB0MG21haWwzLmludGVybmFsLmhvbWV1bml4LmNvbTANBgkqhkiG9w0B
 [delete]AAOCAgEANzr/jRcEd5BF2QqF+X8deq4Xxp1tN9lFgji38C5ixNJ+Busq9Sk5
 [delete]O7YYJQbSf5K14eZyC1jaNEOEwqgzFiM1HRWL1HCca3EM7TXUoH8sMXS1Ng
 [delete]M5oyfQcFWZYa22CtKQANQEX5l7EYNkr0yvD/YnP02l3hk1jZr+3pszCW6Iw
 [delete]vabHMYcAXus+iOGgws788QsMaqzoZwla1AaacZ98s0lFAR0xdRiuXCHUFz
 [delete]meS5sK+med95/z+Mb6ShJzC7KAi1nfZk9CoNHUHVxMis5Cr+GT7MoIvhQ
 [delete]8fkiANQQoEgam37lyHezPKyc6iLxW4ag2PWKrZa2+3pyTg/6aHKxZR325z
 [delete]kcdwKYo/eUGaN1tNmsY638N4hCz01FHHKr97W0m4u5wtwKBo4/5Gy9e5nG6
 [delete]khOyjfOz6VYvZHNqDaqGJwsxitxSGGDc8bA+9d73RCOFuztwVrKYg5OJ
 [delete]Ei5C9gWzee7AmoGpgxOrYjgBrx4nuBw71EFzgKSOZqxUxSNiLuGAx+oVd2
 [delete]Z4EAPsa90ZNb0mLGagAuTAdccekOqPVnyZrqiINelY7fpAAUvO9rgTSB9A
 [delete]RxUydTgY1jyBtoXjp59HMVbCkAtOtX43NqIhPYJNPeSoyw/5SU=
 -----END CERTIFICATE-----

=====Get Root CA's=====

Root CA certs are found here  :  https://www.cacert.org/index.php?id=3

Do the following on the server:
 
 [ su - root ; cd /opt/zimbra/ssl/zimbra/commercial/ ]
 wget http://www.cacert.org/certs/root.crt
 mv root.crt commercial_ca.crt

=====Verify=====

Let's verify all is good.

 [ su - root ; cd /opt/zimbra/ssl/zimbra/commercial/ ]
 /opt/zimbra/bin/zmcertmgr verifycrt comm commercial.key commercial.crt

Giving something like this:

 ** Verifying commercial.crt against commercial.key
 Certificate (commercial.crt) and private key (commercial.key) match.
 Valid Certificate: commercial.crt: OK

======Errors - Double check time======

* Date  [is it wrong?]
** Install ntpd if it's not
** Stop ntpd                               :  
*** <pre>/etc/init.d/ntpd stop

- Set time with :
  - ```
  ntpdate us.pool.ntp.org
```
- Confirm time change :
  - ```
  date
```
- Confirm hardware clock time :
  - ```
  hwclock
```
- Sync hardware clock time :
  - ```
  hwclock --systohc
```
- Confirm hardware clock time :
  - ```
  hwclock
```
- Start ntpd now :
  - ```
  /etc/init.d/ntpd start
```

Deploy CA

[ su - root ; cd /opt/zimbra/ssl/zimbra/commercial/ ]

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

Restart the webserver

su - zimbra
zmmailboxdctl restart

Ajcody-Notes-SSLCerts

Contents

SSL Certificate Issues

Actual SSL Certificate Issues Homepage

Resources For SSL Certificates

Bug & RFE's Related To SSL

Ldap Doesn't Start After Cert Changes Or Upgrade

Deploy CA

Restart the webserver

Products

Support

Learn

Community