Random PDF attachments showing the paperclip in Outlook 2007 but the attachment doesn't show in the email.

Recently in our domain with Exchange 2007 and using Outlook 2007 we are seeing randomly an issue which involves pdf attachments.  Clients send our users an email with pdf attachments and the users can see the paperclip indicating that there is an attachment but when the email is opened up it does not show the attachment.  In one instance if you save the email and check the file size it is 1 MB so it is definitly carrying the attachment.  If the open the email in Outlook Express the attachment is there and it will open.  If you check OWA in Internet Explorer 8 the attachment is there but it gives an error of "Internet Explorer cannot download attachment.ashx from web.company.com (where company is our company name). Internet Explorer was not able to open this Internet site.  The requested site is either unavailable or cannot be found.  Please try again later."  When we try OWA from Chrome the attachment will open up fine.

When you forward the message to an outside email address and they recipient opens the email they can see the attachment.

We go through postini for spam protection.

As I said this is a random issue but it seems to be happening more and more and really turning in to an issue.

Any help would be appreciated.
LVL 6
Neadom TuckerAsked:
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Neadom TuckerAuthor Commented:
Just want to give an update on this.  The issue ended up being an Exchange Server setting.  The ShowInlineAttachment setting was set to False.  I changed this to True and had the users have the emails resent and the attachment is showing up now.

I figured I would post this in case anybody else runs in to this issue.

Thank you everyone for your help.
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databoksCommented:
Do they use anyform of Outlook Shield(antivirus)?
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Neadom TuckerAuthor Commented:
No.  We use Vipre Enterprise but have Email Protection disabled.
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databoksCommented:
Does it happen randomly on differnt kind of users or is only on some specific users?
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Neadom TuckerAuthor Commented:
It happens randomly on different users.  We are starting to experience more and more users that this is happening to.
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databoksCommented:
Just to clarify is this only happening on PDF attachments?
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Neadom TuckerAuthor Commented:
Yes this is only on pdf attachments that I know of.  They are the only ones being reported as an issue.
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Neadom TuckerAuthor Commented:
One more thing.  They use an Outlook plug-in called Nuance PDF Converter 7.0.  When the email is highlighted you can click on Nuance PDF and open the attachment with this fine.  You just can't see any evidence of the attachment at all besides the email file size and the paperclip.  Again, it is totally random.
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Neadom TuckerAuthor Commented:
Nevermind this being only with pdf attachments.  I had a user today say that an email with 4 .jpg attachments wasn't showing the attachments in the email.  But it was showing the paperclip and he could view the attachments on his phone.
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databoksCommented:
Have you tried making a new profile for the user? See if this helps.
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Neadom TuckerAuthor Commented:
I have tried to make a new profile for one of the users.  The issue still remained.  More and more users are reporting the issue.
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databoksCommented:
Okay. I will get back to your later today.

I will try find some solutions for you. Sorry for the late response.


I will give this attention.
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Neadom TuckerAuthor Commented:
Any word on this yet databoks?
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Neadom TuckerAuthor Commented:
None of these solutions worked.  I have absolutely no clue on this one.  This has been happening for about a month and a half now.
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databoksCommented:
Try request attention. I am also lost on this one.
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Neadom TuckerAuthor Commented:
Thanks for trying.
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Jeffrey CoachmanMIS LiasonCommented:
Does the size of the PDF play a role in this?

Where are these PDF's coming from?

If some are created by Adobe Acrobat and some are created by "Joe's Discount PDF Creator", ...then this might be part of the issue

Finally I have had issue with Old an New PDF files
Some newer apps may not like "Old" pdfs created in Acrobat1.0
Similarly, some older apps might not recognize AdobeX PDFs
;-)

Jeffcoachman

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Neadom TuckerAuthor Commented:
I originally thought that it was just .pdf files but I have seen .jpg files also intermittently are having this issue.

The size of the attachment plays no bearing.

The files are coming from a myriad of places: mac's, android devices, outlook 2007, outlook 2003.  This seems to have no bearing either.

We have tried to open these emails in Outlook 2003, 2007 and 2010.  The paperclip is there but the attachment does not show up when you open the email.  It is there in OWA.  In OWA in IE the attachment does not open but it will open in Chrome, Firefox, etc.
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Jeffrey CoachmanMIS LiasonCommented:
Then this seems to OWA, IE issue...

Are you all up to data on the OWA Server, Workstation Windows, and IE with Service packs/patches?
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Neadom TuckerAuthor Commented:
Yes.  When we first found out about this issue that is one of the first things that we checked.
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Jeffrey CoachmanMIS LiasonCommented:
Then I'm stuck too.

Time to contact MS directly I suppose...
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puppydogbuddyCommented:
Your description is indicative of blocked attachments based on MS's list of  "unsafe file extensions".

see this link:   http://office.microsoft.com/en-us/outlook-help/view-open-and-save-attachments-HA001231953.aspx
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Jeffrey CoachmanMIS LiasonCommented:
puppydogbuddy,

Yeah, I thought so too at first, but they also noted that some .jpgs were not working either.

But I guess it is worth investigating, just to see what the settings are...

Jeff
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puppydogbuddyCommented:
Hi Jeff,
Long time, no see.   Good to see that you are still participating on EE.   In reference to jpg, I think that I saw or read somewhere, that Microsoft became aware that malicious code/viruses could be piggybacked behind a jpg image, and that image files were added to the unsafe attachment list.......but I can't remember where I saw it, or found any documentation to support that... I will look again.

PDB
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Jeffrey CoachmanMIS LiasonCommented:
... Good point, yeah I saw several articles where you could "embed" things into jpg  image files...
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Neadom TuckerAuthor Commented:
Still unsure about what this could be.  The firm where this is taking place does not have a MS support agreement but they just merged with a larger firm that I believe has a support agreement.  I am sending an email to their Exchange support personnel tomorrow to find out.  I will post updates here in case someone else comes across this issue.
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Jeffrey CoachmanMIS LiasonCommented:
Great.

You can now accept your own post as the solution

;-)

Jeff
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Neadom TuckerAuthor Commented:
Worked with a Microsoft Exchange Technician to come up with the solution.
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WatershedTechCommented:
Had this issue too.  Thanks all for your hard work.
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