On Tue, 2 Feb 2016 13:28:14 -0600
[sigh] It is an ISP issue. My apologies for cluttering up the mailing
list.

Jeremy


Jeremy Volkening <[email protected]> wrote:

> After successfully testing an identical configuration on another
> system on another network, it seems likely that this issue is somehow
> related to my particular local network configuration (NAT'd behind a
> quasi-static public IP) which results in the remote MTAs refusing the
> connection, and is not at all OpenSMTPD-specific. This at least sends
> me in a fresh direction of research/inquiry. Any suggestions would
> still be welcome, however.
> 
> Jeremy
> 
> On Tue, 2 Feb 2016 12:14:46 -0600
> Jeremy Volkening <[email protected]> wrote:
> 
> > Hello,
> > 
> > Is there any way to force OpenSMTPD to use SMTPS on port 465 for
> > outgoing relays (without using a smarthost)?
> > 
> > I'm trying (and failing) to configure OpenSMTPD to relay outgoing
> > mail (v5.4.4 on OpenBSD 5.8 and also tried v5.7.3p1 on Linux). Here
> > is my barebones smtpd.conf:
> > 
> > listen on localhost
> > accept for local deliver to mbox
> > accept for any relay
> > 
> > I've tried many other possible configurations. Perhaps revealingly,
> > if I set it to forward via a smarthost I have credentials on with
> > explicit SMTPS:
> > 
> > accept for any relay via smtps://<relay>.com
> > 
> > then things work fine. If I don't explicity specify SMTPS then this
> > fails as well with similar debugging output. Network monitoring
> > indicates that when mail is successfully sent via smarthost, the
> > connection is initiated on port 465. However, with other
> > configurations all connection attempts are made on 25 and the
> > destination servers never respond. I have tried this with multiple
> > destinations. Name resolution succeeds in each case, but the
> > destination servers never respond on port 25.
> > 
> > I know from past experience with Exim that I must explicity tell it
> > to use SMTPS for outgoing relays. I suspect that I'm having the same
> > issue here, but I can't figure out how to configure this behavior on
> > OpenSMTPD. I can set 'smtps' as an option on the 'listen' control
> > word but not on 'relay'. Any help or suggestions would be greatly
> > appreciated. I can attach full debugging output if requested, but
> > again it seems clear from the network logs that smtpd is repeatedly
> > trying to connect to remote hosts on port 25 with no response, while
> > perhaps it should be trying on port 465.
> > 
> > Thanks,
> > Jeremy
> 
> 


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