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Outlook 2010 attachment problem

Posted on 2011-09-22
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Last Modified: 2012-05-12
a user has a few contacts he cannot send attachments to, each on different domains (1 gmail, 1 hotmail, etc).  another user in same office, using same exact setup can send same attachment to same contacts, so it doesn't seem to be the recipients error.  Attachments range from tiffs to pdfs to office docs.  The email is received, but the attachments are removed.  Checked all settings and I can't find anything set differently.  I already looked at the contact entry and set it to send emails as plain text instead of html in case it was a translation issue, but that didn't fix it.  Our office is running exchange 2008.  
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Question by:HuckTx
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by:johnb6767
ID: 36580946
Any chance this user is in the recipient's Blocked Sender's list? They receive these emails in the Inbox?
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by:HuckTx
ID: 36581156
Yeah, they receive them in their inbox, not junk folder.  He can send them regular emails and does so often.  this is an Engineering/Architecture firm, so there is a lot of correspondence going back and forth.  Its only when he attaches a file and even then, they still get the email.  
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by:John Hurst
ID: 36581247
I have this issue at a client and the cause is the AntiVirus software on the email server. When I send an email to an internal colleague with an attachment, she gets the email but the attachment is blocked and the same in reverse. Check your email antivirus and see if that is what is blocing things. (I am not responsible for this server)
 ... Thinkpads_User
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by:HuckTx
ID: 36582491
I will have to have my supervisor look at the exchange server, but I don't think the problem is with a virus scanner because the other employee in the next office over is running on the same software, same exchange server, and same domain and he can send to the same people with the same attachments and they don't get removed.  It seems like its something specifically with this user.  I've reinstalled Outlook too.  My theory is that its something in his contact entry for those few contacts, but I can't track it down.  I already tried setting those specific contact entries to sent only as plain text rather than html or rich text, but that didn't help.  
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by:HuckTx
ID: 36582495
and he can send attachments to other addresses, its just a select few.
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by:johnb6767
ID: 36584874
Could you create another Email Profile for him, and test?
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by:Amit Khilnaney
ID: 36587481
By default, Outlook 2010 classifies several file types as Level 1 and blocks files that have those extensions from being received by users. Examples include .cmd, .exe, and .vbs file name extensions. As an administrator, you can use Group Policy to manage how a file type is categorized for e-mail attachment blocking. For example, you can change a file type categorization from Level 1 to Level 2 or create a list of Level 2 file types. There are no Level 2 file types by default.

You can configure Outlook 2010 attachment security settings by using Group Policy and the Outlook 2010 template (Outlk14.adm). Most of the attachment security settings are the found under User Configuration\Administrative Templates\Microsoft Outlook 2010\Security\Security Form Settings\Attachment Security. Settings to prevent users from customizing attachment security settings and to use Protected View for attachments received from internal senders are found under User Configuration\Administrative Templates\Microsoft Outlook 2010\Security. Attachment security settings cannot be configured by using the Office Customization Tool (OCT).

Fore More Details

http://technet.microsoft.com/en-us/library/cc178961.aspx#BKMK_Level1

And there is something about Protected View Also...
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by:Krishnamanoj83
ID: 36592772
Hi,

As you mentioned issue having with few contacts, try to narrow down the issue, ask the user to send one attachment to external contact and also your collegaue to send same attachment to that contact and see if both of them in that mailbox not showing in that case its likely to be the policy/filter setup to bloick or strip certain attachments, if thats the not the case only one user is having issue then definitely some issue with his PC corrupted with virus, so please scan the user PC and also ask the user to test the same from different PC


Regards,
Krishna
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Author Comment

by:HuckTx
ID: 36599172
Yeah, we've already tried that and the second user can send attachments to the clients the first user can't.  so the attachments can be sent and received and both users are on the same network with the same policies.  User one can send attachments to all the other addresses he attempts, its just 3 or 4 contacts that he can't send attachments (but the emails do get delivered) to.  The pc has been checked by scanners, but we can scan again.  Thats why we were thinking its a contact list thing.  I guess we should delete those users from his contacts and see if he can send them.  That might be the one thing we haven't tried yet.  Just for a little more info, we've been fighting this for a couple of months now.  Thank you to all those responding, while not having hit the nail yet, it spurs other ideas too.
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by:Krishnamanoj83
ID: 36600119
Hi,

Did you ask the user to test the same from different PC? also ask the user not pick from contact instead type the contacts and check the same, also you mentioned you are using exchange 2008 which is not there, is that 2007 or 2010?

Regrads,
Krishna
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Author Comment

by:HuckTx
ID: 36601367
Oops, sorry about that.  We are on Exchange 2010.  I was thinking of our 08r2 server when I was typing.  I have not had the user log into a different PC using his name, but that is a good suggestion.  Thanks!
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Author Comment

by:HuckTx
ID: 36815496
update: I had him send an email with attachment through our web portal.  The client received the file.  So the problem has to be with his local installation.  I just had him delete one of the contacts out of his address book completely and send to that address with attachment.  
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Accepted Solution

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HuckTx earned 0 total points
ID: 36817832
problem solved.  It was either a setting or corruption in contast list entries.  I had him remove them contacts out, reboot, then recreate the contacts and the attachments get delivered perfectly.  Strange but true.  Thanks to all those that responded and help inspire me to approach this from a different way.
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Author Closing Comment

by:HuckTx
ID: 36908481
The problem was with the contact entry.  They had to be completely deleted before it would send the attachment to the client.  Once deleted, we were able to recreate them and the attachment was able to be delivered.
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