I had the need to setup Outlook to connect to an SME Server 8.0 recently and at first glance it seemed easy enough but it did not work as expected.

The primary issue appears to be that Outlook does not like to play with the SME Server SSL or Ports without being shown the way.

The end result is a step by step guide that I have published over at the WrenMaxwell Knowledgebase complete with screenshots of each step.

I suspect that this may well apply to other self-hosted servers beyond SME Server and kept the text generic for that purpose, but if you are trying to get your SME Server to work then the first thing to do is make sure that the imaps and smtps ports are open on the firewall and on the SME server.

The only other thing that needs doing is aligning the server name with the external hostname and the self-issued SSL certificate.

It was interesting that setting up a couple of portable devices, an iPhone, iPad, and Android all worked with the SME Server connection without any specific settings being required, the server was just accepted and worked from the get-go.  Microsoft Outlook, however, seems to raise barriers.

I did reference this Microsoft article KB286197 as a preliminary to this process and found it lacking for the options of secure SSL connections and certainly it has the basics but insufficient detail to guide an appropriate outcome for an SME Server connection.

The SME documentation over at contribs.org is also lacking a bit of input and I might try to help out there if I can make some time.