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

Jim Ohlstein jim at
Thu Mar 23 13:39:14 UTC 2017


On 3/23/17 8:21 AM, Arthur Chance wrote:
> On 23/03/2017 03:25, Jim Ohlstein wrote:
>> Your entire question is ridiculous since Sendmail will never be
>> useful for retrieving email from a remote server. Ever. To do that
>> you need a POP/IMAP server. That was my point. Still is.
> If you'd been paying attention you'd have noticed lines in his mail like
>> telnet localhost 25
> which is rather a clue that he's talking about the sending side rather
> than the receiving side.

If you'd been paying attention, you'd have noticed lines his initial 
post to the list (emphasis mine):

I just want to use a self-signed certificate so I can *get my email from 
my FreeBSD mail server to my cell phone*.

This is rather a clue that he's talking about the receiving side rather 
than the sending side.

I don't see anything about sending, and from the content of his 
responses that insisted that it was working for this purpose, and I'm 
not convinced the issue was not lost on him. I think until last night he 
was of the belief that he was using Sendmail to retrieve his email. In 
my first email I informed him that he cannot use Sendmail to retrieve 
email because Sendmail does not act as a POP3 server or as an IMAP 
server. His exact response:

I have news for you.  Unless this feature was just removed from 
sendmail/FreeBSD, it should work.  It WAS WORKING until November 2016.

That doesn't sound to me like someone who actually knew the difference. 
Hopefully he does now.

>> I only suggested you consider another agent since this one is
>> proving difficult for you to configure. I never said you "had to" do
>> anything, but you will need more than Sendmail to use your phone's
>> email client.
> I'm sure he's aware of this, but is having problems *sending* mail
> securely via SMTP and sendmail.

 From where did you glean this? See above.

>> But keep going, you're doing great.
> Quite possibly a little better than some other people.
> [Much snippage]
>>>> "Never argue with a fool, onlookers may not be able to tell the difference." - Mark Twain
> [Except for that. :-)]

Cute. Rather sophomoric, but still cute.


Jim Ohlstein

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

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