Unable to send to Gmail accounts

Question

HI,
I'm running into a problem with the ability to send to gmail accounts from Exchange. After moving to Exchange 2013 I can send to gmail accounts only sporadically. I can never send to multiple gmail recipients and often even one will give a delayed error.
When looking at the delivery report I get a error of '[{LRT=};{LED=};{FQDN=};{IP=}]'. I've checked the SPF records recreated them using Microsoft's SPF Generator. I've even removed the SPF record all together.
I did tests using smtpdiag utility and everything checks out SOA is fine local domain TCP and UDP checks out, Remote records to gmail are good, and the MX servers ( 5 responded).
Am I missing something? Like I said I can send at times and at other times it delay's and then fails.
This is ONLY happening on gmail.
I've waited online for hours for google support and they told me a tech would get back to me ( which of course they never did).
Any Ideas for this would really be appreciated!
Thanks!
J.J.
J.J.

Answer 1

Hi JJ,
Does this issue occur on a specific time?
How is the impact in you org, only one user or all users?
If only one user has this issue, I suggest creating a test user and mail enabled it on the previous version Exchange server, then migrate to Exchange 2013 and send to Gmail for testing. 
According to the NDR message, it seems the email message in the queue expired. The sending server tries to relay or deliver the email message. However, the action is not completed before the message expiration time occurs.
This message can also indicate that a message header limit has been reached on a remote server, or some other protocol time-out occurred while communicating with the remote server.
Found some information for your reference:
4.4.7: This message usually indicates an issue on the receiving server. Check the validity of the recipient address, and determine if the receiving server is configured correctly to receive messages.
You may have to reduce the number of recipients in the message header for the host about which you are receiving this error. If you send the message again, it is placed in the queue again. If the receiving server is available, the message is delivered.
Please also use following tool to check whether you are in the Gmail Blacklist:
http://mxtoolbox.com/blacklists.aspx
Disclaimer:
Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make sure
that you completely understand the risk before retrieving any suggestions from the above link.
For the detailed reasons on the receving server side, I suggest asking Google for help so that we can get more professional suggestions.
Thanks
Mavis
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