My certificates are self-signed, as per the instructions in the howto. When you send to that mailserver using SSL Outlook prompts you with:
"The server you are connecting to is using a security certificate that could not be verified.
A certificate chain processed, but terminated in a root certificate which is not trusted by the trust provider.
Do you want to contiune using this server?"
If you choose YES then you can send through the mailserver quite happily. But as soon as you quit Outlook and restart it, you get the warning again. Which is obviously a PITA.
The internet is absolutely riddled with similar questions (search google for Outlook root certificate "could not be verified") but I just cannot find a definitive answer which matches the steps I've gone through in the howto.
i.e. the HOWTO tells me how to setup the server, but I need to final steps to create the certificate for import into the client.
The stuff at http://ohno.mrbill.net/pipermail/lin...il/001100.html
looks okay, but I still can't seem to get the right combination of ciles and parameters.