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Exchange 2003 All Outgoing emails with attachments fail

Posted on 2009-02-11
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Last Modified: 2013-11-30
OK...  So today my exchange server has stopped working with email that contain attachments all other email is fine inbound and outbound but Emails I send with attachments or emails trying to be sent to me with attachments fail. I have tried sending an email with an attachment from gmail to my server the email never shows up in a any of the queues and no ndr or anything in the gmail inbox. Now as far as trying to send email from outlook i can send emails just fine without attachments but even if i add a 1kb text file and send the email I instantly get an NDR from my server

Your message did not reach some or all of the intended recipients.

      Subject:      test

The following recipient(s) cannot be reached:

     <email>@gmail.com on 2/11/2009 6:44 PM
            The e-mail address could not be found.  Perhaps the recipient moved to a different e-mail organization, or there was a mistake in the address.  Check the address and try again.
            <server.domain.local #5.1.0>

If i try to send the email to myself I get the same thing.. just with it saying my Display name instead of the external email


Now another interesting thing to note if I load up OWA and try to attach a file it gives me an HTTP 500 Service Error and in outlook if I try to open the sent email with an attachment it tells me Cannot Open This Item: Unknown Error..

There is no messages in the event log about any of this te mail queues are empty. it just makes no sense..
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Question by:HFComm
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Expert Comment

by:winthropj
ID: 23618707
Any recent changes to the virus protection on this box?
Remove the "Show only friendly HTTP errors" setting from IE on the advance tab in Internet Option. It will give you the specific error.
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Author Comment

by:HFComm
ID: 23618733
The only changes made recently was i was having some NetBios issues the server has multiple ips on a single nic i bound dns to only one ip and I disabled the the Firewall built into the Trend Micro OfficeScan 8 client. Otherwise the server has OfficeScan for OS level and file scanning and GFI MailEssentials and MailSecurity for virus and spam scanning.

After turning off friendly error messages it still says the same thing

HTTP/1.1 500 Internal Server Error when hitting attach.
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Author Comment

by:HFComm
ID: 23618738
For testing I disabled all of OfficeScan and all the GFI Mail Suite tools and still had the same issues.
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LVL 5

Expert Comment

by:winthropj
ID: 23628686
Not getting much help.....
I've been looking around but nothing quite fits. I'll keep at it though. I know what it's like to be in the hot seat for an email server.
Disk space is OK?
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Expert Comment

by:winthropj
ID: 23628840
Have you double check the allowed attachment size?
In Exchange Sys Admin - Global - Message Delivery Defaults.

The NDR from Outlook is odd since it references not finding the email account instead of something about attachment size. It is also strange that the gmail message doesn't come through. I can't think of much that would tie all of these together.
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Author Comment

by:HFComm
ID: 23628982
The array with the exchange mailboxes has 121 gigs free and the size limit is set for 10 megs here is an interesting one the ndrs in outlook 2007 say as above not found but the ndr if i open it on my Windows mobile phone says everything the same but at the bottom says the recipient's may be full or the email address may be incorrect.
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Accepted Solution

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HFComm earned 0 total points
ID: 23664240
Well I was able to solve this myself I decided to try and reset the OWA virtual directories and the problem has went away ever since.. not 100% sure on the issue but it is fixed for now..
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