I have an domain account configured with Ipower.com. If I use an email client such as Evolution, the mails arrive as expected. However if I use Outlook 2007 (as everybody in this company) the mails only arrive if the destination belongs to the same domain. That means when the destination is a gmail address, for example, the test email falls into a sort of black hole... (I check the spam folder, and they aren't there)

This is just a simple ipower setup, nothing of Exchange or something like that.

What else can I do to isolate and fix this issue? This is driving me nuts because in other email client with the same exact configuration in the same machine, everything works well and I need to fix the thing in Outlook.

I enabled the Outlook logging feature (*) and the server says everything goes well, but not really.

2010.05.05 15:46:00 SMTP (smtp.example.com): Begin execution
2010.05.05 15:46:00 SMTP (smtp.example.com): Port: 25, Secure: no, SPA: no
2010.05.05 15:46:00 SMTP (smtp.example.com): Finding host
2010.05.05 15:46:01 SMTP (smtp.example.com): Connecting to host
2010.05.05 15:46:01 SMTP (smtp.example.com): Connected to host
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 220 ESMTP Wed, 05 May 2010 16:46:00 -0400: UCE strictly prohibited
2010.05.05 15:46:01 SMTP (smtp.example.com): [tx] EHLO vm
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 250-bosauthsmtp01.eigbox.net Hello vm []
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 250-SIZE 34603008
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 250-PIPELINING
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 250-AUTH PLAIN LOGIN
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 250-STARTTLS
2010.05.05 15:46:01 SMTP (smtp.example.com): <rx> 250 HELP
2010.05.05 15:46:01 SMTP (smtp.example.com): Authorizing to server
2010.05.05 15:46:01 SMTP (smtp.example.com): [tx] AUTH LOGIN
2010.05.05 15:46:02 SMTP (smtp.example.com): <rx> 334 xxx
2010.05.05 15:46:02 SMTP (smtp.example.com): [tx] xxx
2010.05.05 15:46:02 SMTP (smtp.example.com): <rx> 334 xxx
2010.05.05 15:46:02 SMTP (smtp.example.com): [tx] *****
2010.05.05 15:46:02 SMTP (smtp.example.com): <rx> 235 Authentication succeeded
2010.05.05 15:46:02 SMTP (smtp.example.com): Authorized to host
2010.05.05 15:46:02 SMTP (smtp.example.com): Connected to host
2010.05.05 15:46:02 SMTP (smtp.example.com): [tx] MAIL FROM: <*****>
2010.05.05 15:46:02 SMTP (smtp.example.com): <rx> 250 OK
2010.05.05 15:46:02 SMTP (smtp.example.com): [tx] RCPT TO: <*****>
2010.05.05 15:46:03 SMTP (smtp.example.com): <rx> 250 Accepted
2010.05.05 15:46:03 SMTP (smtp.example.com): [tx] DATA
2010.05.05 15:46:03 SMTP (smtp.example.com): <rx> 354 Enter message, ending with "." on a line by itself
2010.05.05 15:46:04 SMTP (smtp.example.com): [tx] 
2010.05.05 15:46:04 SMTP (smtp.example.com): [tx] 
2010.05.05 15:46:04 SMTP (smtp.example.com): <rx> 250 OK id=1O9lTn-0005Yj-89

(*) In Outlook, Tools -> Options -> Other -> Advanced Options -> Enable Logging (troubleshooting) and the log file is in %TEMP%\Outlook\OPMLog.log. This text file records commands and responses by Outlook and the server.

  • Can you confirm that it is not ending up in the gmail addy's spam folder? Not sure how familiar you are w/the inner workings of email but does everything look as you would expect in the headers for the email you send/receive w/in your domain? Can you send email from gmail to your email client? – malonso May 5 '10 at 14:30
  • The emails do not arrive to the spam folder. And I can send email from gmail to the domain, and the arrive correctly. – Alex. S. May 5 '10 at 14:46
  • What do your log files show? – Ben Quick May 5 '10 at 15:15
  • sorry Ben, which log files?, outlook log files? where are they? if you mean log files of the server, I don't know, because is a domain managed by ipower. – Alex. S. May 5 '10 at 15:46
  • 4
    What does ipower say? One of the reasons for outsourcing email is that the outsourcer gets to deal with these kinds of issues. They should be able to find the messages is question and tell you what is going on. If they are not helpful, find another provider. – tomjedrz May 5 '10 at 15:54

The last line is an OK from SMTP server, that means it's done so the issue is not on your end! You should contact the domain provider.

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Are both email clients using port 25? Maybe evolution is configured to use port 25 but has a box checked for "TLS/SSL Enabled" which is causing it to send over 587 (seen this in eudora).

Their documentation asks to use 587 as outgoing. This is a counter intuitive solution because your log shows the email going out fine, but its worth a shot.

Source: http://www.ipower.com/info/systemnotice.bml?id=5702

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