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 -- You received this mail because you are subscribed to [email protected] To unsubscribe, send a mail to: [email protected]
