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Email with attachment fails to come through

Posted on 2009-03-31
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Last Modified: 2012-06-27
One of our customers is trying to send an email to us with an attachment. When he tries he gets the following error. He is able to send emails without the attachment, and is also able to send the same email to his personal email address. The attachment size is 1MB with a .zip extension. Both of which normally work fine for us. I have tried to find out what this error actually means without luck. Any help would be greatly appreciated

The e-mail system was unable to deliver the message, but did not report a specific reason.  Check the address and try again.  If it still fails, contact your system administrator.
            < mx2.sendercompany.com #5.0.0 smtp; 5.1.0 - Unknown address error 554-'Message Denied: Restricted attachment (Mode: normal)' (delivery attempts: 0)>

Setup:
MS Server 2003 Std x86
Exchange server 2003 std
All incoming email is routed through spamsoap and then forward to us
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Question by:siftd106
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by:daraghmccormack
ID: 24028593
mx2.sendercompany.com server is causing the problem.  Contact the spamscan company and see if they have changed the attachment scanning policy or check what is contained in the zip file and the attachment scanning can normally check the zipped content to ensure it is not dangerous.  So it could possibly be the zipped file types are blocked
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by:siftd106
ID: 24028654
I do not think it is the spamscan company. Whenever they block something they send an email saying that they blocked it and let you pass it through if it is not spam. Thus it would not result in a unable to deliver message. What would cause you to think it is the sendercompanies server that is causing the problem?
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by:matt_str
ID: 24028962
There is an option to block some file extantions in exchange, try to send another attachment and see if it works.
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by:daraghmccormack
ID: 24033576
Outlook can also blcok attachments, check your message tracking to see the size when exchange delivered it to the mailbox.  There is a registry key to turn off attachment blocking in outlook
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by:siftd106
ID: 24033754
For a temporary fix I had our customer post to our ftp site. However I then took the file and was able to send it to my personal email address. Then from there I was able to send it back to my work email. For another test I took a .zip file which contained a .exe and sent it from my personal email to my work email. My personal email returned it as undeliverable, with the exact same error that our customer received. I then looked inside the .zip from our customer and and it did not contain anything that I thought should be blocked, and I asked the customer if the file had been changed since when he tried to email it the first time and when he posted it to the ftp site (thinking that he realized what was happening and then removed the offending file(s) from the zip), he said the the file was the same.

I also checked the message tracking and it showed no record of that email.

The above would leave me to believe that it might be an error on the customers side, but if that is so why would he be able to send it to his personal email?
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by:daraghmccormack
ID: 24033927
Is the server that is mentioned in the NDR your Exchange server?
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by:siftd106
ID: 24033982
No it is not, it is the senders server.
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by:daraghmccormack
ID: 24034033
Are you sure its not the AV Scanning server?  If its the senders server then his NDR shouold be different to the one that you got from your personal account?
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by:siftd106
ID: 24034058
The server that is mentioned in the ndr of my personal email was my personal server. And the server mentioned in the customers email is there server? It is not the AV company, I just talked to them and they would not send Exchange NDRs.
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by:daraghmccormack
ID: 24034136
If its the senders servers giving the NDR, its not really a problem on your server.  I suspect it is a problem with the file content.  .exe are blocked by alot of content filters.  Do you have a personal Exchange server for your email?  If so do you have any AV scanning products installed? Maybe try sending a different .exe?  The NDR states its restricted content, so the sending server is refusing to send it due to it being blocked content.
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by:siftd106
ID: 24034203
My personal email is an exchange server with no AV scanning. I tried sending a .exe and this is the NDR that I recieved.

 There was a SMTP communication problem with the recipient's email server. Please contact your system administrator.
  <exchangeserver.personaldomain.com #5.5.0 smtp;554 Message Denied: Restricted attachment (Mode: normal)>

So what you saying is that my personal server and our customers server refuse to SEND attachments that of certain types?
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daraghmccormack earned 500 total points
ID: 24034334
thats what the error says.  Check the event logs on your personal Exchange server as this may give you more information on why it has given the NDR.
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by:daraghmccormack
ID: 24034406
The NDR codes you have posted are also differnt which indicated differnet porblems
Original one form customer
#5.0.0 smtp; 5.1.0 - Unknown
One on personal server
#5.5.0 smtp;554 Message Denied
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