SMTP Authentication

I have MIAB all setup and working for most situations. However, I have a few endpoints that cannot send email out using MIAB.

I tried to use Outlook and added the account credentials and everything works as expected. However, when I try to send email via, for example, my pfSense firewall I get an error:

1/14/2019 1:31:14 PM: 220 ESMTP Hi, I’m a Mail-in-a-Box (Ubuntu/Postfix; see
1/14/2019 1:31:14 PM: EHLO
1/14/2019 1:31:14 PM:
250-SIZE 134217728
1/14/2019 1:31:14 PM: AUTH LOGIN
1/14/2019 1:31:14 PM: 503 5.5.1 Error: authentication not enabled

How do I enable authentication? Also, this is a complete upgrade to 18.08 just completed today. All DNS is on the MIAB machine.

Thanks for your help!

You should be on 18.04 not 18.08. Authentication should have been enabled automatically.

In the new version, authentication on port 25 is now disabled. (This is in the changelog. It’s one of the few functionality changes in this release.) If you’re connecting on port 25, that’s probably the problem — you have to connect on port 587 using STARTTLS. If that’s not the problem, let us know!

Oops- you are correct - 18.04. Doh!

Ok - I will check with the application I am using see if it supports a different port.

That was it - all is well - thank you for your help.

You guys rock!


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Did you say that this device was a pfSense firewall?

Yes - but there are actually several devices that I am working with.

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