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Outlook 2007 and Exchange - Mail stuck in outbox...

Posted on 2009-04-28
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I have one user, just one that I know of at least, that when he sends mail with attachments, it sometimes sits in the outbox. He then has to quit out of outlook, re-open and then it usually sends.

The computer has AVG and the e-mail scanning portion of AVG has been disabled to see if this fixes the issue, but it doesn't.

Any ideas?
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Question by:Member_2_4213139
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TonySt earned 2000 total points
ID: 24259367
You said it usually "sends" when he reopens outlook.  That means outlook is configured to automatically send and recieve on open.  You can configure which event happens first, the sending, or the recieving.  By default the recieving happens first and the sending last.  Unless you have configured outlook to send and recieve at a specific interval it will not automatically push the mail from your outbox.  Does it send if he clicks the "Send and Recieve" button on the toolbar ??? If it does then try setting an interval in which outlook will process send & recieve requests.  Also check to see if it is configured to process send and recieve prior to exit.
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by:Member_2_4213139
ID: 24270837
Tony,

Many other e-mails send just fine. We randomly see issues on this system where one e-mail with a small attachment (example, word doc), just sits there in the outbox.

This happened again this morning. He sent quite a few emails with attachments. All of them left the outbox almost immediately, yet after a few messages...this one sat there. Outlook had to be re-opened. This is after a totally fresh/new install.


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by:TonySt
ID: 24271101
It may sound like I'm asking alot of really stupid questions here, but I'm trying to get a picture of this.  Is it isolated to only .doc files, pdfs, xls.. etc.    Also is the document (attachment) he's attempting to send already open in another process.  Like attaching a word document that is already open and minimized by MSWord.  Does the attachment have alot of graphics or pictures. ??
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Author Comment

by:Member_2_4213139
ID: 24281759
Tony,

It's mostly happening on word docs and pdfs
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by:TonySt
ID: 24281847
try increasing the size of the space allocation for temporary internet files.  

Internet Explorer   properties temporary internet files
copies of some attachments are stored there after they are attached and before they are sent
if the folder is too full it drastically slows down the processing speed of moving around files and attachments
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by:Member_2_4213139
ID: 24364113
Tony,

That didn't work. This is happening on another system now. Also, having an issue on one of them when I first start Outlook 2007, it hangs at 33% trying to synch with the Exchange server. If you close out of Outlook, wait about 15 seconds...re-open, then it connects fine.

Any ideas?
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by:TonySt
ID: 24364228
What version of exchange are you running ??? 2003 ??
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by:Member_2_4213139
ID: 24364362
Outlook 2007 with all the latest updates on XP Pro. This is really frustrating!
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by:TonySt
ID: 24411735
Sorry for the long time since my last response to your problem, I have off on calls and not in the office much.   I have been thinking about your problem though.  I am beginning to think that his outlook is losing contact with the exchange server and his outlook is going "offline".   In recent weeks I have been seeing quite a few authentication issues between Outlook 2007 and SBS 2003 with Exchange 2003.  My guess is that his Outlook (perhaps even others) are losing conact with the exchange server.  Can you try this...   On his system, under TCP/IP settings, change one of his DNS servers to the IP address of the Exchange server, and Edit his HOSTS file to list the IP/address and name of your exchange server.
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by:TrackBerry
ID: 24546430
A couple of our users have been seeing this problem very sporadically, including me.  We are currently migrating from Exchange 2003 to Exchnage 2007.  All of our users have Outlook 2007 at this point except for about 25.  On my own computer I have had Outlook 2007 for some time.  Shortly after my mailbox was migrated from Exchange 2003 to 2007 I noticed my Outbox would start to hang for no apparent reason.  My work around has been to close Outlook and reopen, which always fixes the problem.  I see the problem happen with emails that do not have any attachments.  The next time it happens I will explore more avenues before working around the problem.
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by:dpcsit
ID: 35084165
One work around for the user is to move the email from the outbox back to the draft section and then open the email and resend it. We are working this issue from a timing aspect, we started seeing this after installing AVG 2011 and we think that a combination of the server being busy and AVG slowing the email processes down might be causing a timeout. We upped the outlook 2003 timeouts to 90 seconds to see if the issue goes away.
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