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  1. #1
    5 Star Lounger Vincenzo's Avatar
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    Messages stuck in Outbox

    On my wife's Outlook 2003 on Vista, occasionally a message does not go out, it remains stuck in the Outbox and then all messages after it do not go out either. Telling Outlook to Send Now does not help, I just need to delete the stuck message, then the others go through, even ones that are from the same email account.

    Any ideas?

    Thanks

  2. #2
    New Lounger keysailor's Avatar
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    You may want to check the addresses in the To: box, if an outgoing message has a malformed email address, it will sit in the outbox forever. Some common problems include spaces in the email address (such as before/after the @ sign) or an improper domain suffix (such as .con versus .com). If this only happens intermittently, it may only happen if she emails someone in her addressbook, and the addressbook entry is incorrect.

    Malformed email addresses can also happen when you are typing an address into the email form's To: box, and mis-type it. Outlook then remembers that mistake, and happily repeats it for you when you next try to type that address.

    Hope this helps!
    Last edited by keysailor; 2011-04-14 at 10:57.

  3. #3
    5 Star Lounger Vincenzo's Avatar
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    Good idea, but sometimes when this happens I am able to make the message go out by opening it from the Outbox, then clicking the "from account" dropdown, and changing it to another account to send from. Then it goes out, and other ones that are backed up, which are being sent from the same "problem" account, will go out successfully then, even though their "from account" has not been changed. It seems like some temporary issue with that account causes the one message to get stuck, and it blocks the others from going out.

    Thanks

  4. #4
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    Do you notice any send/receive errors?

    Joe

  5. #5
    New Lounger keysailor's Avatar
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    Ahh, that's a critical piece of the diagnosis puzzle (Outlook has more than one mail account)! My previous advice was based only on what you'd posted. With this new info...

    If the stuck emails are all being sent out through the same mail account, you may want to check the Outgoing Mail settings on that account. Two common areas that make sending email difficult are outgoing port (SMTP) number, and Outgoing E-mail authentication:

    1. The default sending port is 25 - this should only be used when sending email out through your ISP's account - that's the ISP that you are currently using to access the internet. Most ISP's block email sending through port 25 for any email other than their own. So the easy solution is to use an alternate port (the two most common are 587 and 2525). To change this, open your Control Panel, then type "Mail 32-bit" in the search bar, then open the Internet Email Settings for the account in question, go to the Advanced tab and change the outgoing server (SMTP) port from 25 to 587 or 2525.
    2. Many ISPs are now requiring you to authenticate sending mail. If the mail account in question isn't used often, they may have instituted an authenticated sendmail policy. Simply follow the instructions above, and go to the Outgoing Server tab in the Internet E-mail Settings window and enable authentication (likely using the same settings as the incoming server will work fine).
    Give #1 a try and then try sending email out through that account to see if it goes ok. If that doesn't work, do #2. If neither work, you may want to look at the help files from that email service provider (they may have a specific port to use).

    Btw, both these items are due to ISP attempts to stop junk email.

  6. #6
    5 Star Lounger Vincenzo's Avatar
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    This email account requires port 25. I tried other ports on a different computer, one running Windows Live Mail on Win 7, and mail does not go out if set to port 587 or 2525.
    Also, I've checked in the past with Comcast about port 25. They told me that I should not use port 25 on my comcast email accounts, but on other accounts it is fine. (but my experience with comcast is that if I call three times on an issue like this, I'll get 3 different responses).

    By the way, this problem of messages getting backed up in the Outbox only happens about once a month, not a regular occurance.

    Outgoing Server requires authentication is already checked.

    Joe:
    No, there are no error messages when this issue occurs.

    Thanks
    Last edited by Vincenzo; 2011-04-14 at 17:13.

  7. #7
    5 Star Lounger Vincenzo's Avatar
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    hold on, ignore what I wrote about trying other ports on that account on another computer. I've just changed it back to 25 and those are not going out on the Win 7 computer. Something else is going on here, possibly because I am out of town, using a different ISP.
    Last edited by Vincenzo; 2011-04-14 at 17:35.

  8. #8
    5 Star Lounger Vincenzo's Avatar
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    Ok something else is going on with the Win 7 laptop that I have with me, that I was using to test the feasibility of your idea. It is not sending any email on that account, from my present location.

  9. #9
    Star Lounger MarkAtHome's Avatar
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    Quote Originally Posted by Vincenzo View Post
    This email account requires port 25. I tried other ports on a different computer, one running Windows Live Mail on Win 7, and mail does not go out if set to port 587 or 2525.
    Hi Vincenzo -- you might wish to contact Comcast again. When I was a subscriber, they told me to change the port to another one (might have been 26, but I do not remember), as scammers, spammers, etc. started using other people's port 25 connections to do their dirty work.

    I had my domain host change my ports as well.

  10. #10
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    Follow-up.
    I changed the outgoing port to 587 and it now is operating correctly. Bad advice from the Cablevision helper. But I still believe that it was screwed up by some infection. Thanks to Keysailor (post #2)


    I have the same problem. I noticed that the date stamps are 14 Apr. This happened to me on 18 Apr after an MS update. The Outlook lost its way and I had to reinitiate with ISP (Cablevision/Optimum). All came back EXCEPT output sending, which stuck in Outbox. After help with CV, they finally recom'd reinstalling but I think that something else happened. What --malware? I cleaned with Avast and Malwarebytes and they finally showed clean.

    Graham346
    Last edited by Graham346; 2011-05-02 at 21:08. Reason: Tried and fixed problem.

  11. #11
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    Did this problem get resolved? I don't see an answer

    If there is too many messages in the "Sent Items" folder it will cause messages in the outbox to become backlogged. Since this happens about once a month and then apparently goes away I would guess that Auto Archive is clearing messages from the Sent folder and fixes the problem. I simply move sent messages to a personal "saved sent" folder to fix it.

  12. #12
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    Sometimes this happens because the connection with your smtp server is slow, and it times out. the whole thing gets confused, because the mail is half sent, so cannot be re-sent again, nor has it been completed. What I do is disconnect from the network (internet or LAN), Cancel Send and Receive, move the message to Drafts folder and then re-send when connected again. Normally that solves the problem, and it just flies out.

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