Hi,

> On 9 Dec 2015, at 19:15, Russell Sutherland <[email protected]> wrote:
> 
> I have tried to configure Apple Mail (Version 8.2) to send/relay using user 
> authenticationto my opensmtp server (mail.fqdn.com):

works like a charm here.

> Here's what I have in the smtp.conf file:
> 
> pki mail.fqdn.com certificate  "/etc/mail/tls/smtpd.crt"
> pki mail.fqdn.com key          "/etc/mail/tls/smtpd.key"
> 
> ...
> 
> listen on egress tls pki mail.fqdn.com auth-optional hostname mail.fqdn.com
> listen on egress port submission tls-require pki mail.fqdn.com auth hostname 
> mail.fqdn.com
> ...
> 
> 
> I can get this working using Thunderbird but not Apple Mail. The email 
> clients seem to have upteem options re. certs and SSL and TLS etc. Has anyone 
> got this going??


You have to configure Apple Mail to use SSL, explicitly set the port to 587 and 
authentication to “password”. Apple Mail then tries STARTTLS before using SSL.

hth,
Alex
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