Solved Help needed with OpenSMTPD

That error seems to come from your SMTP server and means that the server encountered a network problem when trying to connect to the target server.

Do you need a DNS server? Well, yes but no, that server must not necessarily be on a particular machine. One well proven approach would be to have a DNS "relay" (correctly, a forwarding server) like unbound on your gateway system (I think it's 192.168.1.1 in your case). But - and careful, that's important! - every host in your network incl. your mail server needs to know (and have access to) a DNS server.

So, concrete, for your situation:
  • Be sure to have some DNS server available and reachable, either on your gateway or some external server like you ISPs DNS server.
  • Be sure that every host in your network knows about that DNS server (you can set it in /etc/resolv.conf)
You can test it by, for instance, host [URL='http://www.google.com']www.google.com[/URL]

P.S. The error you mentioned seems to indicate a network problem rather than a DNS problem.
 
Thank you rmoe,

I've got a laptop somewhere I can use. I'll install a fresh install of FreeBSD and see if I can spot where the problem is. I really appreciate your time in assisting me here.

Fred
 
First of all I would like to say a big thank you to all the people on the forum that have tried to help me with this problem. Now for the solution. The problem has got NOTHING to do with my network setup or FreeBSD in general. I had to spend more than four days to work out that the problem is on the Gmail side. In order for it to work you must enable access to less secure apps on your Gmail account.

Here is a screenshot: https://www.dropbox.com/s/t9ch6yqh52le9pw/Gmail.PNG?dl=0

I really hope this will help other people out there:)
 
Bumping this because I ran into the same issue with OpenSMTPD but on OpenBSD. You have to turn on the "access to less secure apps" in Google account settings as noted but it will take up to a half an hour until that setting actually takes effect. Your test mails will keep getting rejected until the setting is truly in effect.
 
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