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Large emails being sent multiple times to same recipient in Outlook 2003

Posted on 2007-07-25
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Last Modified: 2011-09-20
Hi,
We have a client that regularly sends emails using Outlook 2003 to multiple recipients using both the To and CC fields.  This has been happening since he got his new computer maybe 6 months ago.  Sometimes the email will end up being sent to one or more of the recipients 10 or more times.  When this happens, one or more of the remaining recipients won't receive the email at all.  Also, the email never ends up leaving my client's Outbox which probably explains why it keeps being resent.  We've turned off Norton anti-virus and SpySweeper and looked for anything else that might be interfering with the outbound path.  We've also increased the outbound server timeout to 8 minutes.  His outbound server is at SBC/AT&T which now uses SSL although the problem existed before we switched his settings.  It only seems to happen with large emails and, although my client has been very patient, his patience is starting to wear out.  Thanks in advance for your help!
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Question by:SoftwarePilot
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by:thenone
thenone earned 320 total points
ID: 19565759
I suggest repairing the pst file and rebuilding the profile. Export pst first. Delete profile and then create a new one. Then import the pst file again. Some ISP have a limit of how big you can send out as well.
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by:war1
ID: 19565838
Greetings SoftwarePilot !

The problem is likely due to the combination of sending large emails to multiple recipients, using SSL, and antivirus.  For example, small email to multiple recipients or large email to one recipient will get through.  SSL will slow the send process, as well as antivirus check of outgoing email.

The problem also could be that SBC/ATT gets busy sometimes, so sending takes longer. Thus outbound mail gets stuck in Outbox, trying to resend.

Best wishes, war1
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by:SoftwarePilot
ID: 19566087
Thanks for your suggestions.  We'll try rebuilding the profile and possibly reinstalling MS Outlook.  As we've disabled the anti-virus, I don't think there's a connection there.  I know SBC can get busy but this last test we ran caused the 7MB email to be resent 30+ times starting at 5 PM last night and ending at 7 AM this morning.  Seems like they'd have to be reaaaly busy for this to happen.  Since I don't know the internals of email sending, can someone tell me if the email client or the email server is responsible for sending an email to multiple recipients?  It seems like it's the client but this might help diagnose where the problem lies.  Thanks.
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by:thenone
ID: 19566148
ok usually what happens when large files just sit in the outbox for pop it means that the profile is corrupt. That is why I suggested to rebuild the profile. I believe the max for sending out is 10mb. You don't have to re-install outlook. When email is sent out from a client it is routed by dns to the smtp server.
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by:thenone
ID: 19566156
From the smtp server it is routed through dns to the proper mail servers to be delivered to.
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by:thenone
ID: 19566173
Client -------------dns------smtp server------------mx record----------designated mail server
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by:war1
war1 earned 320 total points
ID: 19566236
>> an someone tell me if the email client or the email server is responsible for sending an email to multiple recipients?

The email client's sending computer is usually the problem.  If the email get stuck in Outbox, Outlook would be trying to send it out multiple times.

If SBC/ATT has a then 10 MB limit on emails, the attachment is 7 MB, counting also encoding and text to fill out the remaining 10 MB.  7 MB is right at the border line. But the email could be stuck in Outbox due to large attachment.
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wct296 earned 360 total points
ID: 19571234
You have not stated that there are any bouncebacks or anything... Is there?

Often it may be the SMTP Servers end, and how the email is sent, generally you offload it to your mail server, which will accept it and forward it on to each recipient in turn. If the email is too large (ie; the SMTP server has a size restriction) it will cut the SMTP connection with the email client the moment it knows how big the email is. I'm pretty sure that this does not cause an error bounceback or an error in outlook (sometimes it will show an error in the details - but it depends on the smtp server)..  

I would say that the SMTP server is rejecting it or truncating it (stripping out the attachment and sending the rest), the client never gets an opportunity to send the whole email (including attachments) so it assumes that it is not sent and sends it again... Thats the first thing to check...

The same thing can happen between SMTP servers, but if that is the case, the email would leave the outlook outbox OK.. so I doubt it is that..

What sort of size emails are being sent?
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by:SoftwarePilot
ID: 19575544
The current problem emails are 7 MB in size but they can be larger.  So far, there have been no bouncebacks.  The email simply goes out to one or several recipients multiple times but never makes it to the remaining recipients at all.  The entire email (including attachments) always gets received by the recipient.  I had him forward the above email to my partner and also CC both me and himself.  Throughout the night, I received more than 30 copies of the email but neither he nor my partner received a single one.  I believe he finally deleted it from his Outbox in order to stop it from sending more.  At least that's what he's done in the past.  Thanks.
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by:war1
ID: 19575596
SoftwarePilot,

You Outbox could be corrupt.  To create a new Outbox, you need to create a new PST.
http://support.microsoft.com/kb/829971

Then drag all the emails and contacts addresses to the new PST file. Do not drag the emails from Outbox.
http://pubs.logicalexpressions.com/Pub0009/LPMArticle.asp?ID=52
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by:war1
ID: 19588166
SoftwarePilot, any update?
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by:SoftwarePilot
ID: 19588436
Rebuilding the PST file per above did not solve the problem.  We've also tried uninstalling MSO 2003, cleaning out the registry entries and then reinstalling with no luck.  I don't think I got everything out of the registry, however, as Outlook remembered all the email settings when I started it the first time after the reinstall.  Does anyone know how to completely purge Outlook and its remnants for a reinstall?

An interesting aside is that, while looking through my client's Sent Items folder trying to find the test email we've been using, I noticed that he's sent emails as large as 58 MB in the past.  They haven't changed ISPs since we've been working with them so there must not be a limitation on the outbound email size.

Our next test is to create a new user account on the computer and set up Outlook with the same email settings.  I'll probably get to that on Monday.  Thanks for all your advice!
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by:war1
ID: 19588447
>> Does anyone know how to completely purge Outlook and its remnants for a reinstall?

Account settings are located in registry. Backup your registry. Then navigate to the following key:

HKEY_USERS\S-1-5-21-xxxxxxxx-xxxxxxxx-xxxxxxxx-xxxx\Software\Microsoft\Windows NT\CurrentVersion\Windows Messaging Subsystem\Profiles\Outlook

and delete the account settings there.

>> I noticed that he's sent emails as large as 58 MB in the past.

This may be true in the past. But ISP may have recently change the rule to limit attachment size.  Check with the ISP.

Keep us updated on the account change.
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by:SoftwarePilot
ID: 19618835
Well.... I never will get the hang of this job.  We started down the path of setting up a test user account using our remote-access software but the connection went off line so I couldn't finish.  When the client returned on Monday, he said the problem had been solved and email was coming in and going out at lightning speed.  I asked if he had actually called a client to see if they had received the email and he said that he had.  He's thrilled now (except for my bill) and I'm completely stumped as to why, after 6 months of living with this problem, that it's now all of a sudden working.

My only guess is that, right before I setup the test account, I had completely removed and reinstalled MS Outlook 2003 but after the reboot, I had tested the behavior and it had not changed.  Maybe that actually fixed the problem.  I don't know so I guess I don't know where the points go.  How does that work?  Either way, thanks to everyone for your help.
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by:war1
ID: 19619913
SoftwarePilot, glad Outlook is working properly.
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by:wct296
ID: 19621914
Glad its finally working - If it was me, I would distribute the points across everyone who assisted ... or those who provides the closest answers...

You certainly had a curly one there ;)
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Author Comment

by:SoftwarePilot
ID: 19624132
Done.  And you get the round-up of points (250/3)!  Thanks again to everyone for your help.
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Expert Comment

by:markahays
ID: 20789606
I ran into the same problem with Outlook 2007 and 2003 running on XP.  The issue seems to be linked to the "server timeout" value on the sender's copy of Outlook -- and a bug in the Outlook resend function.  Anything that delays the send process can trip the limit, e.g. emails that have large file attachments, a slow wireless connection, slow email server response, and delays caused by antivirus scans.  This can occur whether the user is linked to an Exchange server, Unix email server or simply connecting to the Web to via an ISP.

The best solution appears to be to increase the server timeout value -- to 5+ minutes if you have a fast connection, or more if the connection and throughput are slower.   (Select your main email account and pick edit/change, then "More Settings" then the "Advanced" tab.)

I hope this is helpful!
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