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Outlook/Exchange 2003 - Certain attachments will not send

Posted on 2005-05-16
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Last Modified: 2008-01-09
We are experiencing intermittent issues with users sending attachments.  We are using Exchange 2003/Outlook 2003.  Problem attachments are not of any particular type or size.  Have successfully sent files larger than the problem files and with the same or different file type.  When sending the attachment through Outlook, the message "Outlook is trying to retrieve data from the Microsoft Exchange Server server.domain.com" then get a message saying that there is no connection to the mail server.  Server pings successfully.  RPC Pings successfully.  Attachments WILL send successfully through OWA.  Have completely uninstalled antivirus and tested with the same results.  Any ideas of what may be causing the issue or what a resolution may be?
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Question by:bccoates
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Expert Comment

by:Sembee
ID: 14023017
Is it always the same attachments? ie can you go to another machine and attach the same file only for it to fail?
Anything special about their name?

Anything connecting the users this is affecting? Same user, different users etc?

Outlook 2003 SP1?
Exchange 2003 SP1?
What is the host OS for Exchange and what Service Pack is it on?

Simon.
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Author Comment

by:bccoates
ID: 14024258
Thank you for the reply.  This one really has me stumped.  I have 3 examples of files that will not send (PDF, WMV, and DOC).  I've been able to send files larger than these examples, so I know it isn't size related.  The same files will not send for any user on any machine.  Have tried changing the file names with no luck.  Running Outlook 2003, no SP.  Running Exchange 2003, no SP.  Server 2003, no SP.  Unfortunately, I haven't been able to find a common thread other than the attachment examples that will not send.  Truly challenging issue.  All other mail is unaffected, thus far.  Have worked through just about every troubleshooting method known!  Looking for help!!!!
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Expert Comment

by:Sembee
ID: 14037399
Any reason why you haven't service packed Exchange and Outlook? Both service packs are rock solid. I actually held up a deployment of Office 2003 waiting for the first service pack.
I can understand why you haven't SP'd Windows, as that is new, but the other two are almost a year old.

Simon.
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Author Comment

by:bccoates
ID: 14039873
Simply a matter of time, or lack there of, on the SP's.  I applied SP1 to Outlook on a system and was still unsuccessful in sending the attachments.  Any thoughts?
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Expert Comment

by:Sembee
ID: 14041403
The problem is that without some kind of pattern as to the trigger of the problem we are just chasing our tails. If you cannot replicate it then working out the problem is very difficult.

Simon.
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Author Comment

by:bccoates
ID: 14042300
We can replicate the issue.  We have examples of 3 files that will NOT send from Outlook, from any user.  The same attachments WILL send through OWA.  Unfortunately, the variables are numerous, but then again, that's why I'm asking the experts :)
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Expert Comment

by:Sembee
ID: 14045468
What is consistent about those files? Same creator, same machine, same OS etc? Is it a long file?
Is it just those three files that cause the problem?

As for replication - could I create files that would cause that problem?

If you open the files, copy and paste the content to a new file, and save the file with the exact same name, does it send correctly then?

You need to rule out whether it is the physical file, its name or its content that is causing the problem.

Simon.
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LVL 7

Author Comment

by:bccoates
ID: 14046704
The files are three different types (PDF, WMV, and DOC) of different files sizes.  Different creators, different machines, same OS (Windows XP Pro).  Currently, I only have the three examples, but other users have reported the same issue but we haven't captured their attachments.  The issue isn't with all attachments though.  90% of email sends without issue.  I was able print the pdf file through Acrobat Distiller to recreate the document and was able to send the new file.  Tried changing file names with no effect.  The video (WMV) file is the most challenging document as it was emailed initially from someone within the company.  Can't put a finger on what may have changed in the system setup that would cause the issue.  Everything is under 10MB, which is what our limit is set at.  Thanks for your continued thoughts, and I'm looking for any direction that I may have missed.
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Accepted Solution

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Sembee earned 2000 total points
ID: 14052552
The only thought that I can come up with is that the files have got damaged in some way, and whatever caused the damage has done the same thing to all the files.
The fact that you were able to recreate the PDF file is a clear indication that the file itself, and not the data is the cause of the problem. I suspect that if you did the same thing with the .doc file then you would find that would send as well.

Tracking down the cause is going to be very difficult. AV would be my instinctive thought - either on the email server or on the machines or file server.

Simon.
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LVL 104

Expert Comment

by:Sembee
ID: 15584414
Just going through some of the old outstanding questions as it is quiet...

Has this problem been resolved?
If you need clarification on any part of the responses above, please post back.

Otherwise you need to close the question by awarding points, or posting in the Support Topic Area (top right corner) with a link to this question asking for the moderators to close the question for you without awarding points.

Simon.
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