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Date: Sat, 02 Nov 2013 20:38:54 +0100
From: Andrea Venturoli <ml@netfence.it>
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To: "R. Scott Evans" <freebsd-questions@rsle.net>
Subject: Re: [Half OT] Mavericks' Mail and SSL
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On 11/01/13 20:12, R. Scott Evans wrote:

> 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?

Thanks again.
Would you mind sending me your .cf file, your FreeBSD, Sendmail, and 
OpenSSL version?
Any other useful config file?

Are you using a self-signed certificate?

  bye & Thanks
	av.