Tag Archives: openssl

Renewing SSL certificates

It is that time of the year when I needed to renew all of my SSL certificates for my web servers and email servers.  This post is a reminder for myself on the steps and commands needed to succesfully renew the certificates, for future reference.

First, check the current certificates and key files.  For CentOS 6, this is located at /etc/pki/tls/private and /etc/pki/tls/certs.

[root@localhost ~]# cd /etc/pki/tls/private
[root@localhost private]# ls -lart
-rw-------. 1 root root 1704 Feb 19  2014 localhost.key
-rw-r--r--. 1 root root 1033 Feb 20  2014 localhost.csr
drwxr-xr-x. 5 root root 4096 Jan 29 15:33 ..
drwxr-xr-x. 2 root root 4096 Feb 16 09:06 .
[root@localhost private]# cd ../certs
[root@localhost certs]# ls -lart
-rw-r--r--. 1 root root    1805 Feb 20  2014 localhost.crt
-rw-r--r--. 1 root root    1757 Feb 20  2014 localhost-chain.crt
-rw-r--r--. 1 root root    1521 Feb 20  2014 localhost-root.crt
-rw-r--r--. 1 root root    5083 Feb 20  2014 localhost-postfix.crt
-rw-r--r--. 1 root root 1005005 Jul 14  2014 ca-bundle.trust.crt
-rw-r--r--. 1 root root  786601 Jul 14  2014 ca-bundle.crt
-rwxr-xr-x. 1 root root     829 Jan 21 01:32 renew-dummy-cert
-rw-r--r--. 1 root root    2242 Jan 21 01:32 Makefile
-rwxr-xr-x. 1 root root     610 Jan 21 01:32 make-dummy-cert
drwxr-xr-x. 5 root root    4096 Jan 29 15:33 ..
drwxr-xr-x. 2 root root    4096 Feb 16 09:09 .

Next create the new certificate signing request (CSR).  Take this chance to create a new private key, with perhaps a higher number of bits and a better algorithm.  This is done using the -newkey, -sha256, and -keyout flags.  The -nodes flag is used to create the new private key without a passphrase (so that the services using the private key can start without needing input from a human).

[root@localhost ~]# cd /etc/pki/tls/private/
[root@localhost private]# openssl req -nodes -newkey rsa:4096 -sha256 -keyout localhost-new.key -out localhost-new.csr
Generating a 4096 bit RSA private key
writing new private key to 'localhost-new.key'
You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
Country Name (2 letter code) [XX]:MY
State or Province Name (full name) []:Kuala Lumpur
Locality Name (eg, city) [Default City]:Kuala Lumpur
Organization Name (eg, company) [Default Company Ltd]:hazrulnizam.com
Organizational Unit Name (eg, section) []:localhost
Common Name (eg, your name or your server's hostname) []:localhost.hazrulnizam.com
Email Address []:

Please enter the following 'extra' attributes
to be sent with your certificate request
A challenge password []:
An optional company name []:
[root@localhost private]# ls -lart
-rw-------. 1 root root 1704 Feb 19  2014 localhost.key
-rw-r--r--. 1 root root 1033 Feb 20  2014 localhost.csr
drwxr-xr-x. 5 root root 4096 Jan 29 15:33 ..
-rw-r--r--. 1 root root 3272 Feb 16 10:05 localhost-new.key
-rw-r--r--. 1 root root 1748 Feb 16 10:05 localhost-new.csr
drwxr-xr-x. 2 root root 4096 Feb 16 10:05 .

Send the CSR file (localhost-new.csr) to the certificate authority, and wait for them to issue the certificate for your new key.  Put the certificate files (including the CA root and chain) in the /etc/pki/tls/certs directory.  Do not overwrite the old certificates yet!  I named them localhost-new.crt, localhost-chain-new.crt and localhost-root-new.crt

Now we need to stop all the services using the old certificates.

[root@localhost ~]# service httpd stop
Stopping httpd:                                            [  OK  ]
[root@localhost ~]# service dovecot stop
Stopping Dovecot Imap:                                     [  OK  ]
[root@localhost ~]# service postfix stop
Shutting down postfix:                                     [  OK  ]

Now rename the old certificates for backup.

[root@localhost ~]# cd /etc/pki/tls/certs
[root@localhost certs]# mv localhost.crt localhost-old.crt
[root@localhost certs]# mv localhost-chain.crt localhost-chain-old.crt
[root@localhost certs]# mv localhost-root.crt localhost-root-old.crt

[root@localhost certs]# mv localhost-postfix.crt localhost-postfix-old.crt

Then it is time to rename the new certificates to take the old certificates’ names.

[root@localhost certs]# mv localhost-new.crt localhost.crt
[root@localhost certs]# mv localhost-chain-new.crt localhost-chain.crt
[root@localhost certs]# mv localhost-root-new.crt localhost-root.crt

For postfix, all the root, chain and host certificates need to be in one file.  Create that file, taking the old file name.

[root@localhost certs]# cat localhost.crt >> localhost-postfix.crt
[root@localhost certs]# cat localhost-chain.crt >> localhost-postfix.crt
[root@localhost certs]# cat localhost-root.crt >> localhost-postfix.crt

Start all the services that was stopped.

[root@localhost ~]# service postfix start
Starting postfix:                                          [  OK  ]
[root@localhost ~]# service dovecot start
Starting Dovecot Imap:                                     [  OK  ]
[root@localhost ~]# service httpd start
Starting httpd:                                            [  OK  ]

If everything is done correctly, this should be the end of the exercise.  Test all the services and make sure everything is working as before.

OpenSSL workaround for Oracle XE wallet

In Oracle, the UTL_HTTP package is used to fetch pages from the internet directly by the database.  For example, using the UTL_HTTP.REQUEST function, the first 2000 bytes of a web page can be displayed:

SQL> select UTL_HTTP.REQUEST('http://www.google.com') from dual;

<!doctype html><html itemscope="" itemtype="http://schema.org/WebPage"><head><me
ta content="Search the world's information, including webpages, images, videos a
nd more. Google has many special features to help you find exactly what you're l
ooking for." name="description"><meta content="noodp" name="robots"><meta itempr
op="image" content="/images/google_favicon_128.png"><title>Google</title><script
window.google={kEI:"X057UtKqGYvprQeorYDgAQ",getEI:function(a){for(var b;a&&(!a.g
etAttribute||!(b=a.getAttribute("eid")));)a=a.parentNode;return b||google.kEI},h
:function(){},kHL:"en",time:function(){return(new Date).getTime()},log:function(
a,b,c,l,k){var d=new Image,f=google.lc,e=google.li,g="",h="gen_204";k&&(h=
k);d.onerror=d.onload=d.onabort=function(){delete f[e]};f[e]=d;c||-1!=b.search("


However, for pages served with SSL i.e. the https protocol, UTL_HTTP will need access to an Oracle Wallet that stores the trusted certificates for the encryption. Attempting to connect without a wallet will result in a certificate validation error:

SQL> select UTL_HTTP.REQUEST('https://support.oracle.com') from dual;
select UTL_HTTP.REQUEST('https://support.oracle.com') from dual
ERROR at line 1:
ORA-29273: HTTP request failed
ORA-06512: at "SYS.UTL_HTTP", line 1722
ORA-29024: Certificate validation failure
ORA-06512: at line 1


An Oracle Wallet can be created by the Oracle Wallet Manager program.  Unfortunately, the Oracle Wallet Manager program is not distributed with Oracle XE.  I think this is because historically encryption has been part of Oracle Advanced Security, a paid optional Oracle feature.  The good news is SSL/TLS encryption is no longer part of Oracle Advanced Security, as per the Oracle 11gR2 Licensing Guide:

Network encryption (native network encryption and SSL/TLS) and strong authentication services (Kerberos, PKI, and RADIUS) are no longer part of Oracle Advanced Security and are available in all licensed editions of all supported releases of the Oracle database.

So far we have established that using TLS/SSL with Oracle XE is not violating any Oracle licensing issue.  We just have to find a way to create the wallet to be used by Oracle XE.  Of course you can run Oracle Wallet Manager from a non-XE Oracle installation somewhere, and transfer the wallet to your Oracle XE installation.  But what if you do not have access to any properly licensed installation of Oracle?

From the Oracle 11gR2 Advanced Security Guide:

Oracle Wallet Manager stores X.509 certificates and private keys in PKCS #12 format, and generates certificate requests according to the PKCS #10 specification. These capabilities make the Oracle wallet structure interoperable with supported third-party PKI applications and provide wallet portability across operating systems.

Therefore, we can use OpenSSL to create a PKCS #12 archive and it should work with Oracle XE.

In Oracle terminology, a wallet is a directory containing a file named ewallet.p12. Therefore, the PKCS #12 file must be named as such.

In this example I will use the Oracle Support web page as the target page.  First, grab the certificate and all the certificates in its chain by using a browser.  In Firefox, this is done by clicking the padlock icon in the address bar, then clicking on ‘More Information…’.

Firefox Page Info - Security tabThen click on ‘View Certificate’

Firefox Certificate ViewerGo to the ‘Details’ tab

Firefox Certificate Viewer - Details tabSelect the certificate at the bottom of the chain (www.oracle.com) and click ‘Export…’.

Save Certificate to FileChange the ‘Save as type’ to ‘X.509 Certificate with chain (PEM)’ and save the certificates to a file.

Transfer this file (mine is named www.oracle.crt) to your Oracle XE server where you want your wallet to be (I chose /u01/app/oracle/wallet).

Now use OpenSSL’s pkcs12 command to create the wallet file using the certificate file as input.  Use the -export flag to create a PKCS #12 file instead of reading one, and use the -nokeys flag to indicate that a private key does not exist inside the input file.  Enter a suitable password when prompted.  This password will have to be provided when using UTL_HTTP later.

[oracle@oraclexe ~]$ cd /u01/app/oracle/wallet
[oracle@oraclexe wallet]$ openssl pkcs12 -export -in www.oracle.crt -out ewallet.p12 -nokeys
Enter Export Password:
Verifying - Enter Export Password:
[oracle@oraclexe wallet]$

Now we can make SSL calls to the Oracle Support website from the database by providing the wallet and password to UTL_HTTP:

SQL> set pagesize 100
SQL> select UTL_HTTP.REQUEST('https://support.oracle.com',null,'file:/u01/app/oracle/wallet','password') Output from dual;

<title>Oracle Configuration Support Manager</title>
<meta http-equiv="REFRESH" content="0;url=/epmos/faces/MosIndex.jspx"></HEAD>