Signed SSL Certificates in OS X Server 10.5
Saturday, December 4th, 2010
Using signed SSL certificates in Mac OS X Server 10.5 is a bit of a black art. In this article I describe how it’s done. Some services, such as the web service, work fine with signed certificates by default. However, the iChat (jabber), iCal (caldav), Mail (postfix/cyrus), and possibly other services do not work properly without some additional work on the command line (“Terminal”).
The problem in OS X Server 10.5 is that the System Admin app fails to provide decrypted private keys, and points some services to a certificate that doesn’t work for that service. The result is that those services will fail to allow connections over SSL.
I will describe how to fix the Mail, iChat and iCal services. The solution is basically the same for them all: decrypt the private key and replace the encrypted version in the combined certificate-key file, then update the service’s settings to use the proper certificate.
Tags: iCal, iChat, IMAP, Jabber, Leopard-Server, Mail, OS X Server 10.5, Postfix, signed certificates, SSL, Sysadmin

I’m just starting work on the deployment of a lab full of iMacs and Mac Minis, and I’m going to document the process in a blog post. Not this blog post — this is just the appetizer :).
This article will add to Rajeev Karamchedu’s excellent post, “