On Tue, Aug 06, 2019 at 07:32:27AM -0600, John Dale wrote:
> STARTTLS
> Normal Password
>
> I don't see these options in Mail.app for OSX.
>
> I've tried updating ports and different combinations of available
> authentication in Mail.app, but no luck. It either times-out or has
> connection denied.
>
> Any recommendations?
Try the "Connection Doctor" menu in MacOS to see the Mac's view of
the SMTP transaction (somewhere among all the noisy IMAP chatter).
You were likely prompted to accept the server certificate during
the first connection.
Mail.app supports PLAIN, GSSAPI and OAUTH. When you double-click
on the SMTP "row" in the "Connection Doctor" view, you get a more
advanced configuration dialogue for the SMTP server settings, in
which under the "Advanced" tab, you can enable "allow insecure
authentication", which may be needed to get "PLAIN" to work.
--
Viktor.
