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

Valeri Galtsev galtsev at
Thu Mar 23 17:17:37 UTC 2017

Sorry about top posting.

Can we, please, close this thread for good?

It sound like the OP has no idea what he is talking about. Being able to
observe things and report them to the community is definitely not
sufficient to make community do system administration of your machine for
you. It usually is assumed that the one asking for help is capable to do
what he is trying to do and has exhausted all resources in serious
attempts to solve the problem he hit himself before asking others for

No offense intended, all I stated above is just my observation (and as
every human I am prone to making mistakes).


On Thu, March 23, 2017 10:00 am, William Dudley wrote:
> 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 ?
> Thanks,
> 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>
> wrote:
>> 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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Valeri Galtsev
Sr System Administrator
Department of Astronomy and Astrophysics
Kavli Institute for Cosmological Physics
University of Chicago
Phone: 773-702-4247

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