troubleshooting Question

Gmail to company Exchange Server delayed

Avatar of krismlj
krismljFlag for Australia asked on
ExchangeSBS
15 Comments2 Solutions1791 ViewsLast Modified:
Hi,

Wondering if anyone has experienced an issue with senders complaining that gmail sent to a company Exchange server is delayed for 1 - 2 days?

Running SBS 2003 with Exchange 2003.  Have an ongoing problem with gmail being delayed.  It is only gmail, every other email is accepted within seconds however any email sent from a gmail account is delayed for 1 - 2 days with the following message:

This is an automatically generated Delivery Status Notification

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipient has been delayed:

     user@companyemail.com

Message will be retried for 2 more day(s)

Technical details of temporary failure:
Unspecified Error (SENT_SECOND_EHLO): Unknown error 18446744073709551615

I have read a number of forums that it may be due to the self signed server certificate, however after installing a new certificate using the SBS internet connection wizard I get the same problem.

I have run a blacklist check and the domain is not blacklisted, the only Spam filter on the server is the Exchange Intelligent Message Filter and the SCL is set to 4 and all archived spam does not show any gmail messages.

The reverse DNS has been set up correctly from the ISP side.

Help with additional troublshooting tips on why only gmail messages are affected would be greatly appreciated?

Thanks,

Lance
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