I have been trying to figure this out as well. I also read that IIS has an SMTP queue builtin and you don’t necessarily need a full SMTP server running on your Windows IIS server to send mail. I enabled the SMTP component in ISS, But I have not been able to get any email notifications still. I have tried all the plugins as well.
I tried alternative mailer and I got a response back from the plugin creator that said I had to read the documentation for Swift. Yet his documentation doesn’t say anything about having to have Swift installed to use his plugin. I haven’t been to happy with some of the plugin support for WordPress. Many of the plugins are not very well documented and it seems to be hard to get help for any of them.
I just want to be able to get the administrative emails out of WordPress. I don’t want to receive email on my server.
I have tried a couple of plugins and none of them seem to work.
Shift This/ Swift
Alternative Mailer
Those are the only 2 that seem to suport encryption to your smtp server because Google uses SSL encryption over port 465.
