We are having issues with SMTP via outlook to the SmarterMail Server and external domains.  Webmail works fine.  This is just from outlook.  The bounceback is immediate.  There is no delay before it bounces.

 

Outlook config:
SMTP Authentication checked - same as incoming mail server
IMAP port: 993
SMTP port: 465
Encryption: auto for both

 

Server data:
Version Checks
Info    SmarterMail Version - 12.3.5318
Info    Hosting Process: w3wp
Info    Pipeline Mode: Integrated
Passed    Microsoft.Net Framework Version: 4.0.30319.18449

 

We understand that the server software needs to be updated, but want to have this issue resolved before we mess with updates.

Bounce Back Examples:

1:
Your message did not reach some or all of the intended recipients.

      Subject:    testing
      Sent:    11/4/2015 1:48 AM

The following recipient(s) cannot be reached:

      <DELETED>@gmail.com on
            The recipient has been deleted or has no e-mail address.
            
2.
Your message did not reach some or all of the intended recipients.

      Subject:    RE: testing123
      Sent:    11/3/2015 3:22 PM

The following recipient(s) cannot be reached:

      '<DELETED>@gmail.com' on 11/3/2015 3:22 PM
            Server error: '550 <<DELETED>@gmail.com> No such user here'

 

SMTP Logs:

[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 220 <DELETED>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] connected at 11/4/2015 12:23:34 AM
[2015.11.04] 00:23:34 [x.x.x.x][1647661] cmd: EHLO LT01
[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 250-<DELETED> Hello [x.x.x.x]250-SIZE 31457280250-AUTH LOGIN CRAM-MD5250 OK
[2015.11.04] 00:23:34 [x.x.x.x][1647661] cmd: AUTH LOGIN
[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 334 <DELETED>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] Authenticating as <DELETED>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 334 <DELETED>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 235 Authentication successful
[2015.11.04] 00:23:34 [x.x.x.x][1647661] Authenticated as <DELETED>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] cmd: MAIL FROM: <<DELETED>>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 250 OK <<DELETED>> Sender ok
[2015.11.04] 00:23:34 [x.x.x.x][1647661] cmd: RCPT TO: <<DELETED>@gmail.com>
[2015.11.04] 00:23:34 [x.x.x.x][1647661] rsp: 550 <<DELETED>@gmail.com> No such user here
[2015.11.04] 00:23:37 [x.x.x.x][1647661] cmd: QUIT
[2015.11.04] 00:23:37 [x.x.x.x][1647661] rsp: 221 Service closing transmission channel
[2015.11.04] 00:23:37 [x.x.x.x][1647661] disconnected at 11/4/2015 12:23:37 AM