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I've got a couple of Mac OS X 10.6.8 Server web servers that run a custom AMP255 (Apache 2.x, MySQL 5.x, and PHP 5.x) stack installed using MacPorts. We've got a lot of Mac OS X Server servers and generally install SSL certs via Server Admin and they "just work" in the built-in services, however, these web servers have always had SSL certs installed in a non-standard location and used only for Apache.

Long story short, we're trying to standardize this part of our administration and install certs via Server Admin, but have run into the following issue: when the certs are installed via Server Admin and referenced in our Apache conf files, Apache then prompts for a password upon trying to start. It does not seem to be any password we know, certainly not the admin or keychain passwords! We've added the _www user to the certusers (mainly just to ensure they have the proper access to the private key in /etc/certificates/).

So, with the custom installed certs we have the following files (basically just pasted in from the company we purchase our certs from):

-rw-r--r--   1 root  admin  1395 Apr 10 11:22 *
-rw-r--r--   1 root  admin  1656 Apr 10 11:21 *.domain.tld.cert
-rw-r--r--   1 root  admin  1680 Apr 10 11:22 *.domain.tld.key

And the following in the VirtualHost in /opt/local/apache2/conf/extra/httpd-ssl.conf:

SSLCertificateFile /path/to/certs/*.domain.tld.cert
SSLCertificateKeyFile /path/to/certs/*.domain.tld.key
SSLCACertificateFile /path/to/certs/*

This setup functions normally.

If we use the certs installed via Server Admin, which both Server Admin & Keychain Assistant show as valid, they're installed in /etc/certificates/ as follows:

-rw-r--r--    1 root  wheel      1655 Apr  9 13:44 *.domain.tld.SOMELONGHASH.cert.pem
-rw-r--r--    1 root  wheel      4266 Apr  9 13:44 *.domain.tld.SOMELONGHASH.chain.pem
-rw-r-----    1 root  certusers  3406 Apr  9 13:44 *.domain.tld.SOMELONGHASH.concat.pem
-rw-r-----    1 root  certusers  1751 Apr  9 13:44 *.domain.tld.SOMELONGHASH.key.pem

And if we replace the aforementioned lines in our httpd-ssl.conf with the following:

SSLCertificateFile /etc/certificates/*.domain.tld.SOMELONGHASH.cert.pem
SSLCertificateKeyFile /etc/certificates/*.domain.tld.SOMELONGHASH.key.pem
SSLCertificateChainFile /etc/certificates/*.domain.tld.SOMELONGHASH.chain.pem

This prompts for the unknown password. I have also tried httpd-ssl.conf configured as follows:

SSLCertificateFile /etc/certificates/*.domain.tld.SOMELONGHASH.cert.pem
SSLCertificateKeyFile /etc/certificates/*.domain.tld.SOMELONGHASH.key.pem
SSLCertificateChainFile /etc/certificates/*.domain.tld.SOMELONGHASH.concat.pem

And as:

SSLCertificateFile /etc/certificates/*.domain.tld.SOMELONGHASH.cert.pem
SSLCertificateKeyFile /etc/certificates/*.domain.tld.SOMELONGHASH.key.pem
SSLCACertificateFile /etc/certificates/*.domain.tld.SOMELONGHASH.chain.pem

We've verified that the certificate is configured to allow all applications access it (in Keychain Assistant). A diff of the /etc/certificates/*.domain.tld.SOMELONGHASH.key.pem & *.domain.tld.key files shows the former is encrypted and the latter is not, so we're assuming that Server Admin/Keychain Assistant is encrypting them for some reason.

I know I can create an unencrypted key file as follows:

sudo openssl rsa -in /etc/certificates/*.domain.tld.SOMELONGHASH.key.pem -out /etc/certificates/*.domain.tld.SOMELONGHASH.key.no_password.pem

But, I can't do that without entering the password. I thought maybe I could export an unencrypted copy of the key from Keychain Admin, but I'm not seeing such an option (not to mention that the .pem options are greyed out in all export options).

Any assistance would be greatly appreciated.

share|improve this question
Keychain should have an option to export the certificate as pkcs12, with a password that you set - are you not able to do so? Do you know where the key file came from? Your CA should never have a copy of it, so I hope it didn't come from them! – Shane Madden Apr 11 '12 at 0:03
Yes, Keychain Assistant allows me to export as .p12 and I can enter no password, but that doesn't get me what I'm looking for (unless there's a way to convert .p12 to .pem). I'm looking to get the private key sans password for use in Apache. – morgant Apr 11 '12 at 14:58

Export the certificate as .p12. Record the password that's used.

Pull the public key out of the .p12 file - it will prompt for the password that was just set in the export.

openssl pkcs12 -in /path/to/exported/cert.p12 -out /etc/certificates/new.pem -nokeys

Check how many certificates are now in the output file; you can open it in any text editor - it may be just the subject certificate, or it may contain the whole chain (the certs in the .ca file that your CA gave you). If it has the whole chain, that's fine - Apache will accept the whole thing in the same file with no problem. If not, then keep using the chain file they gave you.

Then, let's pull the private key as well:

openssl pkcs12 -in /path/to/exported/cert.p12 -out /etc/certificates/new.key -nocerts -nodes

Note that the -nodes flag instructs the command to not use encryption for the private key; this will prevent Apache from prompting for the password.

Point Apache to these new files, and restart. Should be good to go!

share|improve this answer
Oops, looks like we put our answers together at the same time. Thank you very much for the assistance! – morgant Apr 11 '12 at 16:06
@morgant Sure thing! Glad to help. – Shane Madden Apr 11 '12 at 16:13

As Shane hinted at in the comments, one can export the certificate as a PKCS#12 (.p12) file from Keychain Access (with or without a password, naturally password protecting this step is more secure). To do so, you must first launch Keychain Access as the root user, so sudo /Applications/Utilities/Keychain\\ Access &. From there I was able to run the following commands to extract the private key from the exported .p12 file without encryption and put it alongside the encrypted key in /etc/certificates/:

sudo openssl pkcs12 -in *.domain.tld.p12 -out /etc/certificates/*.domain.tld.SOMELONGHASH.key.no_password.pem -nodes -nocerts
sudo chown root:certusers /etc/certificates/*.domain.tld.SOMELONGHASH.key.no_password.pem
sudo chmod 640 /etc/certificates/*.domain.tld.SOMELONGHASH.key.no_password.pem

So I now have the following files in /etc/certificates/:

-rw-r--r--    1 root  wheel      1655 Apr  9 13:44 *.domain.tld.SOMELONGHASH.cert.pem
-rw-r--r--    1 root  wheel      4266 Apr  9 13:44 *.domain.tld.SOMELONGHASH.chain.pem
-rw-r-----    1 root  certusers  3406 Apr  9 13:44 *.domain.tld.SOMELONGHASH.concat.pem
-rw-r-----    1 root  certusers  1867 Apr 11 08:30 *.domain.tld.SOMELONGHASH.key.no_password.pem
-rw-r-----    1 root  certusers  1751 Apr  9 13:44 *.domain.tld.SOMELONGHASH.key.pem

I updated my httpd-ssl.conf file to:

SSLCertificateFile /etc/certificates/*.domain.tld.SOMELONGHASH.cert.pem
SSLCertificateKeyFile /etc/certificates/*.domain.tld.SOMELONGHASH.key.no_password.pem
SSLCertificateChainFile /etc/certificates/*.domain.tld.SOMELONGHASH.chain.pem

Restarted Apache and it works perfectly.

I had glossed over this part of this in my initial question, but to ensure that the _www user is added to the certusers group (which is required for Apache to read the private key since I preserved those permissions), I had used the following command:

sudo dseditgroup -o edit -a _www -t user certusers
share|improve this answer
This information helped us to fix an issue in where it wouldn't assing an SSL certificate to any webserver. After investigation the .key.pem file was missing in /etc/certificates. In this case .cert.pem, .chain.pem and .concat.pem were correctly created in /etc/certificates. And references to a .cert.pem, .key.pem (** this file was missing**) and .chain.pem were inserted into a 0000_any_443_host.domain.tld_shadow.conf file. These 3 lines were copied and pasted into 0000_any_443_.conf. After sudo /usr/sbin/apachectl graceful the web server was serving again. – Pro Backup Nov 25 '13 at 17:06

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