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NDR message with specific attachment

Hi Folks! I have an issue emailing an outside recipient with a specific Powerpoint 2010 file attached. I can email this person without issue if just sending an email without any attachments. I try and send a certain PPT file attached and I get this below NDR back immediately. I wanted to ask if anyone can guess as to why this might occur?? We are mailing from an Exchange 2010 server using Outlook 2010. I am not sure what their setup is aside from having Trend Micro involved. Thanks!


xxx.xxx.xxx.trendmicro.com #<xxx.xxx.xxx.trendmicro.com #5.0.0 smtp; 554 Malformed Email Rejected.> #SMTP#
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mrosier
Asked:
mrosier
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1 Solution
 
Nick RhodeIT DirectorCommented:
Did you try zipping it?
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mrosierAuthor Commented:
I have not yet, I just wanted to see if there was any information out there as to what about the file could cause this since we successfully emailed the same file in the past in previous versions. Also I did scan the file to ensure it is not viral and it is in fact clean. I will have him try that as well, but any idea as to what causes that?
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Nick RhodeIT DirectorCommented:
My 1st impression is not because its necessarily infected, its due to the file being an executable which could toss a red flag when not zipped
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mrosierAuthor Commented:
actually this is a PPT 2010 file. No executables involved. Also, we just tried sending it zipped, and it came back with the same NDR.
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Nick RhodeIT DirectorCommented:
What's the full error message? And just to be sure this message is coming from their server correct?
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mrosierAuthor Commented:
yes that NDR is coming from the recipient server. Below is the full NDR which was then followed by the original message headers. Do you want those as well?

A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.


The following organization rejected your message: xxx.xxx.xxx.trendmicro.com.







Diagnostic information for administrators:

Generating server: zzz.zzz.zzz.trendmicro.com

recipient@emailaddress.com
xxx.xxx.xxx.trendmicro.com #<xxx.xxx.xxx.trendmicro.com #5.0.0 smtp; 554 Malformed Email Rejected.> #SMTP#
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Nick RhodeIT DirectorCommented:
They would have to check their logs in trend micro to see what the issue is.  Could be exceeding the size limit, File limit etc.  They would just have to make an adjustment or whitelist you.  I would contact their support and have them dig into the issue.
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mrosierAuthor Commented:
gotcha, thanks!!
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