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Email with attachment issue.

Posted on 2013-10-24
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Last Modified: 2014-11-12
Hello,

We are facing a rather weird issue.

We are running SBS2008 with exchange.

Everyting runs smoothly, except one thing. When a specific gmail account sends an email, if the email is plain text is proccessed properly, if the email is with attachement it is not delivered. When that guy sends that email to mine and i forward it to the original recipient it is delivered properly. It looks like there is an issue only with the specific sender (gmail) / receipient (exchange account).

Thank you
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Question by:Comp_support
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Expert Comment

by:Rodney Barnhardt
ID: 39598135
Have you tried doing a trace using the Exchange tools to see how it handles it?
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Author Comment

by:Comp_support
ID: 39599743
Hello,

Are there any intructions on how to do that on SBS 2008 ?


Thank you
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LVL 32

Expert Comment

by:Rodney Barnhardt
ID: 39601399
I am not super familiar with SBS, but in the EMC, under tools, should be message tracking. You fill in the information and it shows how the message flows. You could also look at the message queue here and see if there are any stuck.
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Author Comment

by:Comp_support
ID: 39607907
Thank you.  I will check this out and let you know if it works.
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Author Comment

by:Comp_support
ID: 39620846
I did the mail tracking task for the time period i have been informed that there is the error.
There are no results .
How can i make sure that the logging is enabled ?

Thank you
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Rodney Barnhardt earned 500 total points
ID: 39628339
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Author Comment

by:Comp_support
ID: 39638082
Hello,

i checked my options with the ones mentioned in the site. They are ok.
I found out in an article online that i can create a rule in the transport rules and configure something for the emails containing attachemnets to be treatted differently.

Does anyone know something about that?
Thank you
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Author Comment

by:Comp_support
ID: 39647317
Thank you for your support.

The problem was a combination of configurations on Watchguard, exchange server and Eset for mail servers.
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