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URLScan Installed and Now E-Mail Attachments are Blocked?

Posted on 2005-03-26
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Last Modified: 2012-06-27
I'm trying to e-mail a .zip attachment, and I am receiving the response from my Exchange 2003 server listed below. The only thing I have changed recently is I installed URLScan. I'm pretty sure I have it configured correctly for OWA, and even if I didn't I don't think that would be causing SMTP actions like this would it? Nothing about this problem is logged in the urlscan logs either. I've never had a problem with sending .zip files before.

Your message did not reach some or all of the intended recipients.

 Subject:      ********
Sent:      3/26/2005 1:05 PM

The following recipient(s) could not be reached:

  ********@gmail.com on 3/26/2005 1:06 PM
  The recipient could not be processed because it would violate the security policy in force
  <mydomain.com #5.7.0 smtp;552 5.7.0 Illegal Attachment>


Also, this is logged in the Event Log:

Event Type:      Error
Event Source:      MSExchangeTransport
Event Category:      NDR
Event ID:      3030
Description:
A non-delivery report with a status code of 5.7.0 was generated for recipient rfc822;*******@gmail.com (Message-ID <E18DF4A94205CE40B10250A34F5280462921@mydomain.com>).
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Question by:Grime121
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4 Comments
 
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Expert Comment

by:marc_nivens
ID: 13637293
This actually looks like its gmail's fault.  Exchange doesn't have native attachment filtering capability and I know gmail filters zip files that contain exe's.  So, if you're sending a zip with an exe inside (or other types like vbs) I believe gmail will reject it.  If this rejection is taking plae before the SMTP conversation finishes, then it would be Exchange's responsibility to NDR the message.  That would explain why it appears to be an Exchange NDR.  Try password protecting the zip file.

Oh, and you are correct.  URLScan would not have an impact on this type of issue.  And if you wanted to prove further that is gmail you could look at the SMTP protocol log, or run a network sniffer while the message is trying to be sent.
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Author Comment

by:Grime121
ID: 13637439
Ok, that makes sense. Why do you suppose it was logged in the exchange server's event logs though?
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Accepted Solution

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marc_nivens earned 2000 total points
ID: 13637460
The RFC states that a server is not responsible for the NDR until the message is accepted for delivery.  If gmail detected that there was an executable inside the zip before the message was accepted (during the SMTP conversation) and it kicked back the 5.7.0 error without taking the message, then the Exchange server would be responsible for delivering it and that would also have caused it to log the event.
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Expert Comment

by:ITT2006
ID: 14972633
I know this will not solve the Exchange problem but if anyone wants to send an .exe file over Gmail, heres how:  zip the .exe, rar the resulting .zip, now zip the .rar and rename it to .doc
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