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

Jim Ohlstein jim at
Thu Mar 23 01:36:54 UTC 2017


On 3/22/17 8:32 PM, William Dudley wrote:
> I have news for you.  Unless this feature was just removed from
> sendmail/FreeBSD, it should
> work.  It WAS WORKING until November 2016.

That would be news. I guess you have a super Sendmail that listens for 
and accepts POP3(s)/IMAP(s) connections. That would be interesting since 
Sendmail is an SMTP(s) server. I won't bother you again since you are 
clearly more knowledgeable than I.

> On Wed, Mar 22, 2017 at 8:18 PM, Jim Ohlstein <jim at
> <mailto:jim at>> wrote:
>     Hello,
>     On 3/18/17 6:44 PM, William Dudley wrote:
>         A google search does not reveal a useful answer.
>         I just want to use a self-signed certificate so I can get my
>         email from my
>         FreeBSD mail server to my cell phone.  My FreeBSD server runs
>         sendmail.
>         I don't really want to switch to postfix, qmail, etc. etc.
>     I'm sorry to be the one to break it to you after all this time and
>     effort, but AFAIK Sendmail speaks neither POP3 nor IMAP so you
>     cannot use it as an MDA. You can use it to *send* email from your
>     phone, but not to retrieve it. You also can use it to forward mails
>     to another email address from which you can retrieve it, of that's
>     what you want.
>     If you want to retrieve emails using your phone's email client, you
>     will need an MDA. I use mail/dovecot2.
>     I know that you do not want to install a different MTA, but after
>     all this effort I'd suggest trying Exim. TLS is supported out of the
>     box (in the default ports/packages configuration) and is extremely
>     easy to configure [1]. You can use Dovecot authorization [2] with
>     Exim, killing two birds with one stone.
>     [1]
>     <>
>     - see Section 6
>     [2]
>     <>
>     --
>     Jim Ohlstein
>     "Never argue with a fool, onlookers may not be able to tell the
>     difference." - Mark Twain

Jim Ohlstein

"Never argue with a fool, onlookers may not be able to tell the 
difference." - Mark Twain

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