There are a few reasons a message may get stuck in the Microsoft Outlook 365 Outbox. Here are the most common problems and solutions.
Reason 1 – Recent Password Change
Did you recently change your login password? Perhaps Outlook still is working off the old password. Try closing and restarting Outlook. You should be prompted to enter your password again. If that doesn’t work, try restarting your computer to reset everything.
Reason 2 – Message is Too Large
Check to make sure the message isn’t too large. Have a look at the Outbox. If the size for the message is over 5MB in size, it can sit there for a while trying to send. You can let the message sit there and see if it eventually goes or try to reduce the size of the message. If you have an attachment, try compressing the attachment using WinRAR, Winzip, or using the built in Windows method.
Clearing the Item from Outbox
If you want to just surrender and delete a message from the Outbox so that you may resend it, here’s the best way to do so.
- Exit out of Outlook or go to the “Send / Receive” tab and select “Work Offline“.
Select “Start“, then search for “Outbox” in the Start Search area.
- The item(s) in the Outbox should appear in the search. If you want to view and copy the contents of the email before deleting it from the Outbox, you can open it from here. You can also delete it by right-clicking it and selecting “Delete“. It will finally remove the item from your Outbox.
- Now go back under “Send /Receive” and select “Work Offline” again and resume your workday. The message should no longer be stuck in the Outbox in Outlook.
Note: These steps are based on MS Outlook 365 client for Windows 11, 10, 8, 7 and Vista.
Mike L. says
What fixed this issue for me was to disable the .COM add-ins, then re-enable them one at a time, leaving those I don’t use disabled. To do this, go to File->Options->Add-Ins, click the “Go” button next to COM Add-ins,and deselect the add-ins. Close Outlook and restart computer (restarting may not be necessary but I did it anyway just for good measure). Then use same instructions to re-enable add-ins, one at a time.
Frank Zullo says
After weeks of having to restart my PC to send emails, Vaughn Dragland’s fix worked for me. Not only was I able to send the stuck email, but all emails since have been sent without getting stuck. Many thanks!
Christine du Plessis says
Thanks very much for helping to fix an annoying problem.
Steven White says
No this did not work. Outlook is trying to send a ghost email message that does not appear in my outbox! It says Outlook cannot connect to the outgoing SMPT server! Yet I have no such problems sending emails from my iPhone! I’m guessing this is obviously a local PC Outlook issue due to a corrupted email. I do not know how to clear the “link” to the ghost email which was obviously corrupted during sending and has now remained partially sent but does NOT SHOW IN THE OUTBOX!
So bloody frustrating as I cannot send any emails, only receive them!
Mark Cathcart says
It’s also worth knowing that if you get 553 errors when sending, and the email has an invalid email address or similar, deleting it is not enough. At least with Office 2016.
When you delete it from the Outbox, it is in the deleted folder. Even if you “empty” the deleted folder, the problem email will not be deleted, as it has not been sent. And there is the Catch 22. The only way to stop this is to “double click” on the problem email, either fix the address, or delete all the other addresses and add yours.,
Once the email is sent from the deleted folder, it will be deleted.
Julie lewis says
Wy are my emails getting stuck in my outbox never happened before
BrunoJ’s solution from May 6,2019 worked for me, although there seems to be a 30-60 second delay before sending a basic email with no message. I have been all over the internet trying to find a fix for the problem and tried just about every suggestion out there. One little check mark worked.
Thanks for the help.
Diana Brucha says
Thank you Vaughn Dragland! That did the trick for me :-)
Lori Parker says
I don’t even want an outbox! 98% of the time when I hit “send”, it sends. That’s why when an email gets stuck in the mythical “outbox”, I have no idea that it didn’t go out because I have no message that it didn’t go, it isn’t in my drafts, and I normally have no reason to check there. Heck, I don’t even know if it shows up at any other time!
It has caused the delay of sending and/or returning some pretty important emails! Why can’t I just disable it?
Email is repeatedly trying to send undeliverable emails. This interferes with sending new messages. Have tried to follow directions for “working offline” then delete outbox, but nothing shows up in the outbox. I just continually get “trying to and 8 messages. Help!
Hesham G. says
I was having the same issue, and Bruno J is absolutely right. I have checked the add-ins, disabled some of them, and i was then able to send mails normally after that. Thanks a lot Bruno J!
Vaughn Dragland says
None of the above solutions work. (I have tested this many times.) The actual problem is as follows:
If you open the Outbox folder while there are messages waiting to send, the program marks those messages with a weird icon (which looks like a page with a pen) instead of the regular icon that looks like a paper airplane, and those messages get stuck. If you send a message without having the Outbox folder open, it gets sent normally.
To get a stuck message to go, select it and click Forward. The new message will have the correct icon and it will be sent. Then delete the original (stuck) message.
This old bug was gone for a while, but reappeared after a recent Outlook update…
Bruno J says
I was experiencing this problem and have corrected it. Based on what Jennifer Fretwell said on April 18, I thought it had something to do with a delayed send, But that was a coincidental symptom of the problem. It was caused by an Outlook add-in that i have now disabled. Try disabling add-ins one at a time and sending a test message to yourself. You may have to restart Outlook with each add-in tried.
Jennifer Fretwell’s email of April 18th gave me the clue to fix this. She said “… most of the messages are applying an instant delay to send the message at 5pm on the same day which still never happens.”
I checked and this is what was happening to me. Before trying my solution, be sure to delete any pending emails from the outbox that you don’t really want to send. To clear the problem, I took the following steps:
1. Clicked the “File” tab, chose “Options”, and then chose “Advanced” in the left pane.
2. In the “Send And Receive” section, selected “Send immediately when connected.”
3. Created a test message and sent it to myself.
4. In the “Send And Receive” section, de-selected “Send immediately when connected.”
The send now works correctly. I assume an incorrect registry setting was cleared by doing that.
Valarie O Webb says
Mine is doing the same thing. I’m looking for another email program. Outlook is on my last nerve!
Jim Hamilton says
Just installed 2019 on new computer a couple of weeks ago. A real piece of garbage!!! Half the time, the messages arrive at their destination garbled beyond recognition, showing up as a mass of what appears to be computer code. My friends and family are getting REALLY pissed off, as am I. Now, messages just sit in the outbox, going nowhere. Still able to receive. None of the suggested fixes work – ever! Only wanted Outlook and Word, and had to buy the whole bloody Office Suite – what a total rip!!! Wouldn’t mind paying the price if the crap actually worked. How do I get my money back???
Jennifer Fretwell says
None of the above apply and the messages are still getting stuck in the Outbox. Password has not changed, there are no attachments, send/receive doesn’t work because most of the messages are applying an instant delay to send the message at 5pm on the same day which still never happens.
Kathie Thomas says
YOu shouldn’t have to keep going through this process and yet I am, with no explanation why. All the accounts worked in Outlook 2010 but not 2019 with no clue as to why.