Hi Gilles,

I don’t know how far you got with this. I have resolved the issue, cause 
unknown.

First, I actually had 5.4.3 and not 5.4.4. I was certain that I had upgraded. 
Anyway… so I simply shutdown smtpd, upgraded to 5.4.5 and booted it up again. 
Then rescheduling the emails worked fine much better  with proper downgrade.

Hopefully it was fixed by the version change (something in this area probably 
changed as the message formatting was a bit different).

Heres a log excerpt:

May 15 23:08:13 mail smtpd[5853]: smtp-out: Connecting to 
smtp+tls://[REDACTED]:25 (mms.[REDACTED].com) on session c1bf6e17bee0f395...
May 15 23:08:13 mail smtpd[5853]: smtp-out: Connected on session 
c1bf6e17bee0f395
May 15 23:08:17 mail smtpd[5853]: smtp-out: TLS Error on session 
c1bf6e17bee0f395: TLS failed, downgrading to plain
May 15 23:08:17 mail smtpd[5853]: smtp-out: Connecting to smtp://[REDACTED]:25 
(mms.[REDACTED].com) on session c1bf6e17bee0f395...
May 15 23:08:17 mail smtpd[5853]: smtp-out: Connected on session 
c1bf6e17bee0f395
May 15 23:08:19 mail smtpd[5853]: relay: Ok for bc9c69f19a657426: 
session=c1bf6e17bee0f395, from=<[REDACTED]>, to=<[REDACTED]>, rcpt=<->, 
source=192.168.132.233, relay=[REDACTED] (mms.[REDACTED].com), d
elay=2d23m40s, stat=250 ok:  Message 64860805 accepted
May 15 23:08:29 mail smtpd[5853]: smtp-out: Closing session c1bf6e17bee0f395: 1 
message sent.


Thanks for any effort you put into this!

Eric

> On 15 May 2015, at 09:46, Gilles Chehade <gil...@poolp.org> wrote:
> 
> On Wed, May 13, 2015 at 01:27:44PM +0200, Eric Ripa wrote:
>> Okay. So I've looked further into this, the destination MX record contains 6 
>> addresses. The first 5 generates the below TLS IO Error, but the 6th doesn't 
>> seem to be up to respond on SMTP queries. So what I believe is happening is 
>> that OpenSMTPD retries all alternative MX records when TLS is failing on the 
>> first ones.. but then the last isn't up so it lingers with  'Network error 
>> on destination MXs'
>> 
>> Any input on how to do a workaround? Is it possible to force non-tls on 
>> certain destinations or change the fallback algorithm? 
>> 
> 
> I'll have a look today
> 
> 
> -- 
> Gilles Chehade
> 
> https://www.poolp.org                                          @poolpOrg


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