From: lars@beagle-ears.com

> On 2026-01-31 22:03, Lars Poulsen wrote:
>> I know from previous experience, that I should have STARTTLS
>> enabled, because sendmail does not allow passwords to go on
>> plain text TCP connections.
>>
>> I think it must be a problem related to SSL, but sendmail.mc
>> does nbot seem to mention any SSL configuration, and the RedHat
>> sendmail deployment documention is very old and does not discuss
>> where to specify the .pem files.
>>
>> Where should I look next?

On 2026-01-31, Carlos E.R.  wrote:
> use postfix. +1.

I have used sendmail since the late 1980s, with sysadmin
responsibilities since about 1996, and at one time I really understood
the address rewriting rules. So I was reluctant to switch to Postfix,
when I know I had a bsasically working sendmail, but might have lost
some dependency in my upgrade/reinstallation.

But while there is some learning curve required ... I need to look
closely at how Postfix and SSL mesh with each other ... I got it up in
less than an hour, and some of the configuration tables like
relay-hosts even carried over.

But it turned out that the worst of the problems was a firewall
configuration that had gotten broken on the Windows/Thunderbird side
where I was sending from. The TCP connection to port 25 or 587 never
got out of the PC, which was obvious when I loaded up Wireshark on
the PC side.

I have a lot of experience over many decades, but sometimes I overlook
really stupid things, because "I did not touch that part at all, at least
not recently".

--
Lars Poulsen - an old geek in Santa Barbara, California

--- SoupGate-Win32 v1.05
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