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Corrupt PDF Attachments, Exchange 2007

Posted on 2011-10-27
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Last Modified: 2012-05-12
We host a website for people to sign-up for events and athletic teams/sports.  When people sign-up for said sport, an email is sent to that individual with a PDF attachment which is their receipt.  If the person receives the email, the PDF opens just fine and all is right with the world.  If the email is returned to us (invalid email, mailbox full, etc) the PDF is corrupt and we can't open it to print it to snail mail the receipt to the individual.

This occurs across multiple domains: Gmail, Yahoo, Hotmail, Comcast, AOL, Verizon, et al

Now, our website is setup to send email out directly through one of our Barracudas (Spam and Virus Firewall 300) and doesn't touch our Exchange (2007) setup at all.  The email only touches Exchange should it be returned for whatever reason.  Attachments can't be opened via OWA or Outlook (this was tried across multiple machines).

Opening a returned email brings up an error indicating a corrupt PDF file.  I have tried running a PDF "Fixer" on some of these receipts to no avail - the PDF "Fixer" actually says there are no page numbers in the file.  Also, one of our network guys noticed the files which leave are almost twice as large as the files which are attached if the email should get returned.

It's almost as if something is stripping code from the PDFs.

I'm at a loss.

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Question by:jcritzer
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LVL 84

Expert Comment

by:Dave Baldwin
ID: 37041350
I can't find a source for the info right now but I believe that NDR messages do not return the entire content, supposedly only enough to identify the 'problem'.  You're probably not getting the complete PDF back.  You may need to keep a copy of it on your server.
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Author Comment

by:jcritzer
ID: 37044275
Microsoft says:

"Non delivery reports(NDRs) are sent to a recipient when a message he sent could not be delivered by the mail server. When Exchange server sends such a message it attaches the original message to the NDR message. This behaviour can be altered."

What you said makes sense but, as I'm answering to higher-ups on this, does anyone know for sure if this is the case?  The contents of the original email are indeed contained as an attachment but when you open this attachment, it also shows what appears to be a copy of the original PDF attachment, though I'm not sure whether it shows it simply as a record of its presence instead of the entire file.
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LVL 84

Expert Comment

by:Dave Baldwin
ID: 37046070
If the remote mail server is returning these emails, then Microsoft isn't determining what gets sent back.  I know that emails that have bounced from Yahoo don't contain all the pictures I sent.

If you are only getting back half of what you sent, I'd say that's pretty clear indicator.
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LVL 84

Expert Comment

by:Dave Baldwin
ID: 37046075
You could run a test by sending to one of the failing email addresses and include a Bcc: to one of your own email addresses so you would something to compare it to.
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Accepted Solution

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jcritzer earned 0 total points
ID: 37058317
As it turns out, it's a problem with Barracuda.  They even agreed with our assessment.

We currently have an open ticket with the engineers at Barracuda to determine the cause and, hopefully, a fix.  I'll update the thread when we hear back from them.
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LVL 84

Expert Comment

by:Dave Baldwin
ID: 37058382
Glad you found the source of the problem.  I still recommend that you keep a copy of the receipt for reference.
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Author Closing Comment

by:jcritzer
ID: 37105866
We're still waiting to hear back from Barracuda's engineers.  I will update this question at that time.
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