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User can not receive email from one person when it has an attachment.

Posted on 2011-02-28
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Last Modified: 2012-05-11
Hello and thank you for your attention.

This is a very strange situation. This is the scenario/rundown:

Server runs SBS 2008 standard. Exchange is hosted locally on server.

What happening is that any time any of the users @rc.com receive an email from @thefloodgroup.com. The email comes through only if it does not contain an attachment. If the email has an attachment, it's never received by rc users. There is no failed to deliver message returning to sender of any sorts, its as if the email is lost in limbo.

Everyone uses Outlook 2003 to connect to exchange localy. I did check the spam folder in outlook, but if it was being caught by spam filter all emails from the floodgroup would end up there.

There is a spam filtering service where i already whitelisted @thefloodgroup.com domain as safe. Once again if this was an issue, i believe that no email form thefloodgroup would come through.

There is local firewall, but i don't believe that's the issue b/c there are no problems with any other email but w/ only with email from thefloodgroup.

How do i determine what the issue is and if the issue is on our end or @thefloodgroup.com end.

Thank you...
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Question by:loshdog
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5 Comments
 
LVL 8

Expert Comment

by:pmorton23
ID: 35000197
this could be due to an anti virus engine. maybe the attachment is password protected, or encrypted and the AV cannot open it to scan it. the AV could be set to drop attachments it cannot open. we had to create a special rule to allow certain passwrod protected files thru the AV.
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Author Comment

by:loshdog
ID: 35000206
Thank you for your response.

No the attachment is not password protected. Just a simple PDF file.
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LVL 8

Accepted Solution

by:
pmorton23 earned 2000 total points
ID: 35000354
could also be a size issue. if file is over x size then drop it. what is the size of the pdf. can you have the sender try and send a word doc as a test.
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Author Comment

by:loshdog
ID: 35000895
I emailed the sender at thefloodgroup asking to send the exact email that never arrives to me.
I will post once email is received.

Thank you again pmorton23
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Author Closing Comment

by:loshdog
ID: 35047336
All of a sudden email is coming through fine now. I think it might have been a major user error. It all just seemed so weird.

Thank you for your help.
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