[Half OT] Mavericks' Mail and SSL

R. Scott Evans nanog at rsle.net
Fri Nov 1 13:54:27 UTC 2013

On 10/30/13 17:56, Andrea Venturoli wrote:
> Hello.
> Has anyone tried connecting OS X 10.9's Mail.app to sendmail with SSL?
> Server side all I get is:
>> sm-mta[53510]: STARTTLS=server, error: accept failed=0, reason=unknown,
>  > SSL_error=5, errno=0, retry=-1, relay=...
> Client side, the SMTP server is marked as offline, with no other
> explanation.
> Of course it all worked flawlessly until the customer decided to upgrade
> from 10.8...
> I couldn't come a to a conlusion myself, but I'm seeing a lot of threads
> about this out on the net; however, no solution is proposed.
> My guess is either a bug on the client side (as someone goes on to
> suggest) or some exotic variation of the protocol... perhaps I need some
> OpenSSL tweak? Some specific settings in sendmail's config?
> I tried both base's and ports' OpenSSL, but nothing seems to change.
> Any hint is appreciated.
>   bye & Thanks
>      av.
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I didn't think to test this until I saw this email but yeah after 
updating to 10.9 it no longer worked for me either.

My almost identical error was:
Oct 31 16:20:02 mailer sm-mta[88798]: STARTTLS=server, error: accept 
failed=-1, reason=unknown protocol, SSL_error=1, errno=0, retry=-1, 

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.

Oct 31 16:26:39 mailer sm-mta[95592]: STARTTLS=server, relay=xxxxxxxx 
[xxx.xxx.xxx.xxx], version=TLSv1/SSLv3, verify=NO, cipher=AES128-SHA, 
Oct 31 16:26:39 mailer sm-mta[95592]: AUTH=server, relay=xxxxxxxx 
[xxx.xxx.xxx.xxx], authid=XXXXX, mech=PLAIN, bits=0
Oct 31 16:26:40 mailer sm-mta[95592]: r9VKQcLs095592: 
from=<XXXXX at YYYYYYY.com>, size=349, class=0, nrcpts=1, 
msgid=<453C3868-D943-4861-8486-DFF788C7F3BE at YYYYYYY.com>, proto=ESMTP, 
daemon=MSA, relay=...

Hope that helps,

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