Emails Sent from SmartMail Never Received by GMail Recipients but No Delivery Failure
Problem reported by Allen Hoffman - 3/27/2015 at 1:56 PM
I added a new domain to my SmarterMail email server a few months.  It seems that this domain intermittently emails to GMail accounts are never delivered.  As an example I impersonated one of the email accounts that has been sending these emails that get lost going to GMail accounts.  I was on the telephone with the GMail recipient when I sent them a test message from SmarterMail to their GMail account.  They received that message no problem.  Please note they do have a contact setup in GMail with the SmarterMail email address sending these emails to prevent them from going to Junk/Spam.  I sent them a second message with a read receipt request with no attachments and added a 2nd YMail recipient who is also having the same problem.  Neither one of them received the 2nd email.  I didn't get a delivery failure.  The GMail recipient checked the Junk/Spam folder, there deleted folder and every other folder they have but did not receive the 2nd email.  The 1st test email was delivered to their Inbox successfully.  It seems only to happening with GMail and YMail.  We have DKIM setup properly on the domain.  I just can't understand how 1 email can be delivered successfully and a few minutes later the 2nd email is lost in cyber space never to be delivered and never generate a delivery failure.  Obviously the email address is correct if it got delivered successfully the 1st time.  I would also like to note I have another domain on the same SmarterMail server with approximately 250 email accounts and no one on that domain has complained about this problem.
Has anyone ever experienced this problem?  Is there a log file I can check to see if GMail accepted the email?  I would appreciate any suggestions on how to solve this.  Thanks in advance for your help.

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Andrea Free Replied
Employee Post
Hi Allen,
You can review the SmarterMail logs for more details about an email's delivery. It looks like your mail server is running 12.x, so I'll provide the steps for that version.
  1. First you'll need to ensure your log settings are set to Detailed. Log in as the System Admin and click on the Settings icon. Then click on Log Settings in the navigation pane. 
  2. On the Log Detail Levels tab, ensure Delivery and SMTP are set to Detailed. If they already are, you can review your log files. If they're not, change them, then send some test emails to Gmail accounts so you can try and replicate the failed delivery. 
  3. When you're ready to review the log files, click on the Manage icon. Then click on View Logs in the navigation pane. 
  4. You can enter the sender's or recipient's email address in the search string, and enable Display related traffic to get more details about the Delivery or SMTP session. 
Here are the Online Help documents for those two sections of the interface. These will help explain each setting available in those sections.
If you're not sure how to analyze the log results, please feel free to post them here. I hope this helps! 

Andrea Free
SmarterTools Inc.


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