Gmail to company Exchange Server delayed


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



Delivery to the following recipient has been delayed:

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?


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krismljAuthor Commented:
I have read that link, it refers to the server certificate which does not appear to be the problem in this case.
It's a delay but not deliver failed. The messages will be sent and received finally, so I don't believe that's a certificate issue.
You can test this scenario by other email providers however, like yahoo or hotmail, if that's issue still reoccur on those providers and not only GMAIL, check your internet connection provider for more info. I met a similar case before and that client told me the employees cannot get the emails from a biz partner, and the root cause was the internet provider.
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Abbas HaidarSenior Infrastructure ManagerCommented:
is this happening with Gmail only and only Gmail?
krismljAuthor Commented:
yes only gmail.  yahoo mail works, hotmail works, numerous other domains work, the only one that gets delayed is gmail.  have tested with loads of other free email services and commercial domains and they all turn up instantly.  gmail eventually turns up it just gets delayed by about 24 - 36 hours.
krismljAuthor Commented:
have also had the isp check things out.  the domain was originally blacklisted on sorbs database because it was flagged as being in a dynamic address range, this was due to the reverse dns not pointing to the domain name of the server but rather to the isp.  requested the isp to add reverse dns and now everything is ok.  no longer blacklisted, but gmail is still delayed.
krismljAuthor Commented:
I manage a number of other sbs 2003 machines and all are configured with self signed server certificates and none experience any issues with gmail delays. the only obvious difference between the sbs 2003 machines is the isp but after numerous talks with them they feel they have done everything and it is a server config issue!  The ISP did set up and manages the adsl modem/router so not sure what they may have done differently there.  the firewall just has port 25 smtp traffic forwarded straight to the SBS 2003 box, it does not distinguish between email domains.  but if it was a device config or server config problem i would expect it to affect all email not just email from one domain?!
Don't worry about your SBS server and there is nothing to do with the configurations. I think there is something wrong on Google side, the email flow may not be handled in time so you get the incoming message late.
krismljAuthor Commented:
that is my thinking too.  it wouldn't be such a big deal except there are many business partners who use gmail and they place orders via gmail and a delay of 1 - 2 days would mean we would miss their order, so i really need to find a way to fix this.  perhaps looking through the google forums might turn something up other than the link suriyaehnop provided. or maybe someone on EE has experienced this before and knows what is causing it and how to fix it?  Thanks to everyone so far for your contributions.
krismljAuthor Commented:
thanks suriyaehnop, i am working through the process with google and see what they can do.
krismljAuthor Commented:
Just thought I'd update this as it has been a while and I have found a solution to the problem.  This is unique to SBS 2003 or Exchange 2003.  When you create a new certificate using the SBS wizard it does not automatically update the Exchange Virtual SMTP server certificate and it needs to be manually added.  Not doing this can cause the TLS issues I was experiencing with GMail.  This is not the case in SBS 2008 or SBS 2011 as it automatically updates Exchange certificates as well.

more information about the issue can be found here:!topic/gmail/eD2Vm5LacQQ

Hope this helps someone.
krismljAuthor Commented:
I've requested that this question be closed as follows:

Accepted answer: 0 points for krismlj's comment #a38374968

for the following reason:

after extensive toubleshooting and research was able to find a solution to my own problem.  No one on EE was able to provide a solution to this issue.
krismljAuthor Commented:
noticed that there was a link to a similar article posted by another user.  need to allocate points to him too.
krismljAuthor Commented:
needed more information about the certificate.  the article I was directed to did not mention updating the Exchange Virtual SMTP server certificate just the Server certificate.  took a while to find this out.
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