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Problem Emailing to Gmail Email Addresses from Exchange 2013

Posted on 2014-02-13
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Last Modified: 2014-11-12
I have an Exchange 2013 server having issues delivering emails to Gmail addresses (and/or googleapps hosted email). I'm receiving Delivery Delayed error when I check mail queue.

Error: 400 4.4.7

If I do a telnet test to the domain, it comes back OK, but emails are still delayed.

The IP address is not listed on any blacklists.

rDNS is ok.

Not sure what else to check... Any help would be appreciative.
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Question by:IAmDH
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6 Comments
 
LVL 20

Expert Comment

by:strivoli
ID: 39856367
What result do you get when running the SMTP test on your server with www.mxtoolbox.com?
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LVL 3

Expert Comment

by:suribaba801
ID: 39856552
1 Verify whether it will get delivery delayed message when send to others(like hotmail,yahoo).

2 Try to use nslookup to resolve the DNS records of the gmail.

3 enable the protocol logging.It will help you to troubleshoot the issue,the below article for your reference:

http://technet.microsoft.com/en-us/library/bb124531.aspx

Hope it helps
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Author Comment

by:IAmDH
ID: 39860301
@strivoli see photo SMTP Test
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Author Comment

by:IAmDH
ID: 39860348
@suribaba801 I've already seen those steps online...
1. Only domain is gmail I'm unable to email to, but SMTPDiag Results shows connections successful
2. Here are the nslookup results nslookup3. Enabled logging already:
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Accepted Solution

by:
IAmDH earned 0 total points
ID: 39865374
Turns out that google says it's supposedly temporary... Not sure why it would happen like that.

Here's their troubleshooting wizard: https://support.google.com/mail/troubleshooter/2920052?hl=en&ref_topic=3404235

Screenshot of the result... Also looks like the emails are now going through
Gmail Troubleshooter
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Author Closing Comment

by:IAmDH
ID: 39879007
Used GMail troubleshoot
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