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Date:      Fri, 01 Nov 2013 15:12:35 -0400
From:      "R. Scott Evans" <freebsd-questions@rsle.net>
To:        Andrea Venturoli <ml@netfence.it>
Cc:        freebsd-questions@freebsd.org
Subject:   Re: [Half OT] Mavericks' Mail and SSL
Message-ID:  <5273FD23.7090207@rsle.net>
In-Reply-To: <5273EF3F.8040307@netfence.it>
References:  <52718078.8080702@netfence.it> <5272C747.8030805@rsle.net> <5273EF3F.8040307@netfence.it>

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On 11/01/13 14:13, Andrea Venturoli wrote:
> On 10/31/13 22:10, R. Scott Evans wrote:
>
> Hi Scott.
>
> First of all, thanks for your reply.
>
>
>> and I fixed it in my Mac 10.9 Mail by going to "Mail > Preferences..."
>> and under "Accounts" then "Account Information" and selecting "Edit SMTP
>> Server List.." and finally under "Advanced", I changed from "Use default
>> ports (25, 465, 587)" to "Use custom port" with the value of "587".  I
>> didn't change anything on the FreeBSD/Sendmail/SSL server side.
>
> I'm using port 465 and I tried manually setting it, but it did not help.
>
> Using 587, you mean you are using TLS, not SSL, right?
>
>   bye & Thanks
>      av.


I offer both SSL/TLS (465) and STARTTLS (587) to my users. In the Mac 
Mail I don't see an option for differentiating the connection security 
between SSL/TLS and STARTTLS other than specifying the port manually. 
There is a checkbox to Use SSL regardless of what port option is used 
(which I obviously have checked).

Anyhow, I changed the port on my Mac to 465 and it still worked for me. 
  Then again, I also just tried switching it back to the "default (25, 
465, 587)" option for the port and it now works with that also, so I'm 
not sure what is going on?

-scott



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