By Default at least on Mac OS X Snow Leopard, OpenSSL is not configured to use the trusted root certificates. In order to get that working we can follow up instructions from this blog. However, the Gandi root/intermediate certificate thats being used by XChat Azure by default is not being added to Keychain Access of Mac OS X. If we try to enable SSL on XChat Azure it will fail with Connection failed. Error: certificate not trusted.? (27) error message.
Its very simple to resolve this error and I do have to document it since I was able to fix it. What we need to do is visit the Gandi wiki and copy the intermediate certificate which looks like this:
Then create a file gandi.pem in /System/Library/OpenSSL/ and paste the certificate content that was copied earlier. Make sure to change the irc.freenode.net port to 7000 before you connect. Once Xchat is launched next time it should just connect with no issues.