how do I get STARTTLS working with sendmail on FreeBSD 10.3 ?

William Dudley wfdudley at
Thu Mar 23 15:00:09 UTC 2017

Let's assume that I have no idea what I'm talking about.
However, I can successfully report what I SEE.

1. Android's mail app wants to use STARTTLS when it connects to my mail
server, for
whatever reason (send or receive) isn't important now.  It wants it, and I
want it to be
happy, or else it doesn't work.

2. When I telnet to port 25 of my mail server, sendmail does NOT announce
as one of it's capabilities.  This, despite my having all the incantations
*apparently" correct
in my, fresh self signed cert and key file in /etc/mail/certs,
and various other
things that have been suggested/intimated by various sources.

It would be nice to solve the problem stated in the Subject of this
insanely long thread:

Why is my sendmail refusing to announce STARTTLS ?

Bill Dudley

This email is free of malware because I run Linux.

On Thu, Mar 23, 2017 at 10:20 AM, Matthew Seaman <matthew at>

> On 2017/03/23 13:16, Ian Smith wrote:
> > I suggest acknowledging Jim is correct, and figure out what's wrong with
> > your $whatever.  Other contributors including Matthew - whose knowledge
> > is far beyond mine or most people on this subject - perhaps, like me,
> > hadn't twigged that your problem is pick up, NOT sending from sendmail.
> I very nearly asked about the relevance of sendmail to the problem at
> hand, but I came to the conclusion that the OP meant sendmail when he
> said sendmail, even if he did say 'read' rather than 'send' on one
> occasion.
>         Cheers,
>         Matthew

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