Harry Putnam <rea...@newsguy.com> writes:

> Can any of you experienced exim4 hands interpret this output?

Reading RFC-821 would tell you more.

> Did the Authentication work or fail?
>
> [NOTE: Just for the information, my lan is a fake one 2xd.{local.lan} was 
> just invented right
> out of thin air some yrs ago]
> -------       -------       ---=---       -------       ------- 
>
> $ mailx -v -s "TEST $(dtf) $(hostname -f)" rea...@newsguy.com < txtmsg.txt
>
> LOG: MAIN
>   <= ha...@2xd.local.lan U=harry P=local S=569
> $ delivering 1Xauru-0003TT-Fh
> R: smarthost for rea...@newsguy.com
> T: remote_smtp_smarthost for rea...@newsguy.com
> Transport port=25 replaced by host-specific port=587
> Connecting to mail.messagingengine.com [66.111.4.52]:587 ... connected
>   SMTP<< 220 mail.messagingengine.com ESMTP ready
>   SMTP>> EHLO 2xd

That's an invalid helo string.

>   SMTP<< 250-mail.messagingengine.com
>          250-PIPELINING
>          250-SIZE 71000000
>          250-ENHANCEDSTATUSCODES
>          250-8BITMIME
>          250 STARTTLS
>   SMTP>> STARTTLS
>   SMTP<< 220 2.0.0 Start TLS
>   SMTP>> EHLO 2xd

That's an invalid helo string.

>   SMTP<< 250-mail.messagingengine.com
>          250-PIPELINING
>          250-SIZE 71000000
>          250-ENHANCEDSTATUSCODES
>          250-8BITMIME
>          250-AUTH PLAIN LOGIN
>          250 AUTH=PLAIN LOGIN
>   SMTP>> AUTH PLAIN ************************************
>   SMTP<< 235 2.0.0 OK
>   SMTP>> MAIL FROM:<ha...@2xd.local.lan> SIZE=1609 AUTH=ha...@2xd.local.lan
>   SMTP>> RCPT TO:<rea...@newsguy.com>
>   SMTP>> DATA
>   SMTP<< 250 2.1.0 Ok
>   SMTP<< 250 2.1.5 Ok
>   SMTP<< 354 End data with <CR><LF>.<CR><LF>
>   SMTP>> writing message and terminating "."
>   SMTP<< 250 2.0.0 Ok: queued as E25066800A8
>   SMTP>> QUIT
> LOG: MAIN
>   => rea...@newsguy.com R=smarthost T=remote_smtp_smarthost 
> H=mail.messagingengine.com [66.111.4.52] 
> X=TLS1.2:ECDHE_RSA_AES_256_GCM_SHA384:256 
> DN="C=AU,ST=Victoria,L=Melbourne,O=FastMail Pty Ltd,CN=*.messagingengine.com" 
> A=plain C="250 2.0.0 Ok: queued as E25066800A8"
> LOG: MAIN
>   Completed

It worked because the MTA on mail.messagingengine.com is misconfigured
in that it accepts invalid helo strings.

You want to make sure that TLS is actually required before sending the
password.  Otherwise you may end up sending the password over an open
connection.


-- 
Hallowed are the Debians!


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