Email stuck in your outbox? Try this.

"What do you mean you didn't receive it? I sent it last night!" At least you thought you did. Now you're red-faced in a meeting that was set up to review the PowerPoint presentation that never made it to your recipients.

You check your Outbox and there it is.  If you ever find yourself in this situation, here are some reasons why and some steps you can take.

Re-send the message

First try clicking Send All on the Send/Receive tab in Outlook.

 

 Check your Outbox to see if the message is gone.   

Email attachment is too large

A message can get stuck if it includes an attachment that's too large for some email servers to handle. For example, your workplace might limit the size of email messages you can send or receive. That slide deck with lots of pretty pie charts might be the culprit.

Switch to Working Offline

If re-sending the message didn't work, try reducing the size of the attachments and send it again.

To do that, you might first try to either delete or open the message in the Outbox. But that might not work. Here's why. Outlook is really responsive and keeps trying to send any message in the Outbox. You can't open or delete a message if it's doing that. Instead, you'll probably see this message:

 

 

To stop Outlook's wheels from turning, you can go offline. On the Send/Receive tab, click Work Offline.

 

 

 

Once offline, it's easy to fix the problem:  you can open the message, remove the attachment, reduce its size, and re-send it. Or you can delete the message and start from scratch-if of course you have a copy of the attachment.

  

 

Email server is offline

Sometimes Outlook can't send your messages because your email server is offline--whether an email server at work or online. If that's the case, keep working! As soon as it comes online, Outlook will send all the messages in your Outbox in a second or two.

You'll know your server is offline if you see "Disconnected" in the Status bar.

 

 

  When you're up and running, it will say "Connected."

 

 

 

You should be good to go now. For pointers on trimming down attachments before sending, see Reduce the size of pictures and attachments

 

Office Blogs Comments

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  • Outlook 2007 has a bug. If I open a message in Outbox to amend (or sometimes for no apparent reason), Outlook changes the SENT date to NONE and will NOT EVER send the message. I can forward the message and send the forwarded copy (which does not show up as a fwd, but as an original message.) Any comment on this? I then have to go back and delete the original message with NONE as date, which just stays parked in my Outbox.

  • Linda, it must be "by design", as this shows-up in 2010 as well.  The workaround: after you amend the message, instead of just hitting "save" or closing it, hit "send" once again and it will reset the sent date and put the message back on the queue of messages to be delivered.

    But I agree with you, I'd expect this post to cover such an obvious source of frustration in the otherwise excellent Outlook email client ...

  • Another cause can be the server is on line but a network firewall is not allowing outgoing SMTP traffic. A UK client working in Florida had this problem when using a non Exchange account. This was fixed by changing to the TLS/SSL port usually 587 which is available from most email services.

  • So ... what if you are stuck in "diconnecter."  With Outlook 2010 I used a MAPI connection through Outlook Connector -- it still works fine.  But I would like to move up to Outlook 2013 Preview and there when i set up the connection with exchange active synch with the serverr set to  m.hotmail.com it seems to like the connection ... but I am never connected.

  • I HATE THIS LOOK, I WANT MY OLD HOTMAIL ACCOUNT RESTORED.  I DONT LIKE THE FORMAT, THE COLORS, ITS HARD TO FIND ANYTHING I ONCE HAD DUE TO THE CHANGE.  NOT TO MENTION JUST TO GET INTO THIS DAMN THING TO POST THIS TOOK ME AN HR...REMOVE IT FROM MY COMPUTER, OR I WILL DISCONTINUE HOTMAIL, AND SIGN UP WITH ANOTHER EMAIL SUBSCRIBER.

  • I have a problem.  I changed my Hotmail account to and outlook.com address.  I sent an email to a friend and never heard a reply.  Today she informed me that she had "replied" to my message.  I sent a test message to myself at another one of my email accounts, hit "reply" and somebody else's address -- someone I don't know and is NOT in my address book -- appeared in the "To:" text box.   Obviously, the response would have been sent to them.  Where do I report this problem and have it fixed?

  • Okay ... furthermore, even though I set up an accout for myself, someone else's photo is now attached to my message and identified as "Anonymous!"  I don't know these people!  It is not me!

  • I "upgraded" from Office 2003 to 2010. The only one to gain from that transaction was Microsoft. My Outlook 2010 will not send email. Outlook 2010 installation didn't recognize my Outlook 2003 setup and doesn't recognize my attempts to import my address book and archived mail failed. The "Upgrade" was a reckless marketing scam.

  • I had email stuck in Outlook 2010 , but maybe for a different reason.

    I would write the email, or respond to someone else’s email and click “Send” to queue the email, but either it would NOT turn to italicized text and the date/time would say “none” or it would queue properly, but if I single clicked (NOT double click to open), the italics and date would go away.  If I opened the unsent email and clicked the Send icon, it would NOT re-queue the email.

    I searched the net and found that it was possibly a corrupted .pst file, yet after doing “SCANPST.EXE” on all of the PST files, I had the same problem.  I then found this page support.microsoft.com/.../2652320 and especially noticed “Method 3: Investigate possible issues with add-ins”.  That was my problem.  Specifically, it was the “iCloud Outlook Add-in”.  I had just installed iCloud for the first time with the latest iTunes download.  I unchecked it and all is back to normal.  I rechecked it to see if the problem returned and it did.

    Hope that helps some others who couldn’t send email after installing iCloud.

  • Thank you for posting your comment as I was experiencing the same thing and your post help me resolve my problem.

    It was iCloud.  Thanks again.

  • TO: smyhr

    YOU ARE THE MAN! (figure of speech...you are the man/woman!)

    thanks for your post. that was my problem. now i have to see if I can still use the iCloud address book in Outlook 2010. iCloud is NOT one of Apple's better programs. It has been nothing but trouble.

  • PS: my iCloud address book in Outlook 2010 is still working, so not sure what the iCloud add-in was doing.

  • I have outlook 2007 and BCM. For whatever reason, I started having e-mail issues today. If I create or reply to an e-mail, it stays open in my outbox and cannot be sent. If I leave one ''open'' e-mail in my outbox, I will be able to send all other e-mails I create or reply to. Howebver if I open any e-mail in my outbox It will remain open whatever I do. I have Windows 7. I do not recall having any system updates...

    I unchecked the Icloud add-in and it stil does the same problem.

    Can you help?

  • I haven't been able to send any email for several weeks now from Office Outlook 2007.  This has nothing to do with attachments and all support avenues have been exhausted.  Short of a complete reinstallation (10 days with support) I have not been able to find a solution.  Anyone got any ideas/had this problem.  

    I'm using Hotmail as my email client at the moment which has corrupted all my contacts and I cannot fathom how to synch the calendar/tasks so will not be pursuing this once Outlook is reinstalled.

  • I've just had the same problem - Outlook messages hang in the Outbox, still bold and not in italics.  Tried to visit the KB mentioned by SMYHR but appears unavailable.  Tried System Restore back to when I knew Send worked and then viewed which programs would be affected.  Found it was an iCloud update.  Also found my Restore Points were corrupted.  So, went to Control Panel\Programs and uninstalled iCloud.  All now returned to sweetness and light.  - Hope that works for you too.

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