Thanks to Tim we’ve got a simple workaround to get our own compiled Apache version 2.2.6 running on Leopard with a proper SSL module. The solution is to just use the original mod_ssl module from the original installation. The original mod_ssl module can be found in /usr/libexec/apache2/.

To use this original module the best way possible use these commands:

cd /usr/local/apache2/modules/
sudo mv mod_ssl.so mod_ssl.so.old
sudo ln -s /usr/libexec/apache2/mod_ssl.so mod_ssl.so

Restart the server, uncomment the mod_ssl module in your httpd.conf and restart the server to see it working.

You could also copy the module from its original location but I choose this method because it will benefit from any update that might happen with a security update from Apple.

I can only hope it will also work with a new version of Apache, but we’ll have to wait and see.