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

[William Dudley]

I commented out the lines starting with checkHost, and started stunnel.
It does start, and runs as a daemon.  However, it doesn't seem to DO
anything.

However, that hasn't changed sendmail's behaviour one iota.

As far as I can tell, stunnel is a massive waste of time.

I don't really want to spend months reading all the stunnel docs to figure
out
how to get it to work with sendmail.  Sendmail is hard enough on it's own,
and
I can mostly control sendmail (well, except for the STARTTLS problem.)

Thanks,
Bill Dudley


This email is free of malware because I run Linux.

On Sun, Mar 19, 2017 at 9:53 AM, William Dudley <wfdudley at gmail.com> wrote:

> stunnel fails to start with this helpful message:
>
> /usr/local/etc/stunnel/stunnel.conf:68: "checkHost = pop.gmail.com":
> Specified option name is not valid here
>
> The line it's complaining about is in the EXAMPLE config file.
>
> So this is not going well, at all.
>
> pop.gmail.com is a valid hostname.  I have no idea what stunnel is
> complaining about.
>
> Bill Dudley
>
>
> This email is free of malware because I run Linux.
>
> On Sun, Mar 19, 2017 at 9:44 AM, William Dudley <wfdudley at gmail.com>
> wrote:
>
>> I'll look into this, but a quick read of the stunnel docs, I don't see
>> STARTTLS mentioned,
>> and I thought that was a requirement.
>>
>> Bill Dudley
>>
>>
>> This email is free of malware because I run Linux.
>>
>> On Sat, Mar 18, 2017 at 11:21 PM, Patrick Mahan <mahan at mahan.org> wrote:
>>
>>> On 3/18/17 3:44 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.
>>> >
>>> > Thanks,
>>> > Bill Dudley
>>> >
>>>
>>> Have you considered using stunnel(8)?  I use it to front my sendmail and
>>> other servers that I want to make a secure connection.
>>>
>>> Patrick
>>>
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>>
>>
>