Exchange Server 2010 Can't receive gmails with attachment (or any e-mails hosted by gmail.com with attachment size 50KB or over)

I have a very strange situation where my Exchange Server 2010 can't receive any gmails with attachment size over 50KB. It has zero problems with all other e-mails coming in except hosted by gmail.com. I can receive plain gmails, or with attachment up to 50KB. Anytime a gmail with attachment bigger than 50KB, it will show:

Failed connection to 2001:4860:400b:c01::1a (NetworkUnreachable:00002743)[TargetIPAddress:2001:4860:400b:c01::1a|MarkedUnhealthy|FailureCount:1|NextRetryTime:2015-02-26T22:00:58.693Z]

I involved my Cisco TAC to confirm that my ASA5505 is not dropping/denying any SMTP traffic. Pretty much checked all firewall rules. Absolutely puzzled! Anybody got any ideas?

February 27th, 2015 12:32pm

Hello

tip: Check smtp recive log on exchange server, if not see email from gmail.com go to back cisco or spam filter.

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February 27th, 2015 3:24pm

From my Connectivity Log, I can see gmail.com attempts to establish the connection with my server but in a super short period of milli seconds, it drops off. It just doesn't maintain the connectivity long enough so the attachment gets transferred completely! That explains that a plain gmail gets through, as its size being very small.

It only happens to gmail.com! all other incoming emails are ok no matter how big they are. I don't have any spam filter enabled in the server, and I worked with Cisco for over 1 hour, logging all the gmails coming in, according to them, no block at all!

February 27th, 2015 5:56pm

Hello

Please copy smtp full log when gmail start and finish communication with exchange.

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February 28th, 2015 12:21am

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