How to get out of “Office 365 messages stuck in Outbox” state?

Megha Sharma
Megha Sharma | Updated On - 11 Mar 2022 |

Read time 4 minutes

The Microsoft 365 account is managed in the Outlook application to send/receive emails. The new emails are in the inbox, and the sent emails are in the Sent Items folder. Sometimes, when there is a problem in the email server, then the sent emails are not in the Sent Items folder, but they are stuck in the Outbox folder.

Most of the Office 365 users manage their emails using MS Outlook application. Though Outlook is a professional email client with advanced features, it sometimes happens that a user has sent a mail, but the other user has not received it; and of course, you will not see the item in the Sent Items folder as well. So, where does the email go? The answer is ‘to the Outbox folder.’ It is a folder which stores the sent emails temporary till the traffic of emails is reduced, before moving finally to the Sent Items folder.

It is fine if the emails remain in Outbox folder for some minutes, but if it is taking more time, then your Office 365 messages are stuck in Outbox. You have two options to deal with the emails stuck in the Outbox folder – either delete the emails from the Outbox folder or try to send the emails to the intended recipient once again.

The most common reasons for emails getting stuck in the Outbox folder are poor or no internet connectivity and very large emails, possibly with big attachments. To prevent this situation, you should be careful with internet speed and size of the attachments.

We have some quick fixes which will help you deal with this condition where “Office 365 messages are stuck in Outbox.”

Fixes for “Office 365 messages stuck in Outbox” state
  1. Delete/Send the email stuck in Outbox if it opens without error
  2. Send the emails stuck in Outbox if it does not open and shows error
  1. Delete: First of all, open the email client application for Office 365 and go to the Outbox folder. Click on it and select the displayed emails, right-click on it, and select the Delete option. The stuck emails will get deleted and vanish from the Outbox folder.
  2. Send: Go to the Outbox folder. Now try to open the emails one by one by double-clicking them and then send them using Send option at the top-left side of the interface.

Sometimes the email does not open, but shows errors like “Sorry, we have trouble opening this email item….”. This can happen if Outlook is connected to the server, and the online server keeps trying to send the large-sized emails.

To disconnect email client from the configured email server, just click on the Send/Receive tab at the top of the menu bar and then click Work Offline option.

On the status bar, you can see the status is changed from Connected to Working Offline.

Now, try to open the emails in the Outbox folder again, if it gets opened, send or delete the email as per your requirement.

And, if it still shows the error and fails to open, close the Outlook application. Sign out from the Windows, then sign in and restart the Outlook application.

Now try dragging the emails from the Outbox folder to the drafts folder. Now again go to Send/Receive tab on Outlook and click Work Offline. Then, in the drafts folder, you can access or open the emails; click the Send option to send it directly to the recipients.

Note: If the emails contain large attachments, then use Save All option to save them to a network or shared location. Then copy the link of the folder path (of the shared network where the attachments are stored). Paste this link to the email content and remove the attachment from the email. Then, send this email to the recipient avoiding any further issue.


If you can remove the issue related to the emails stuck in the Outbox folder through the manual methods, it is okay. If the problem remains in the system, you should Kernel Office 365 Backup & Restore software. It will save the mailbox data in a PST file, and when your account shows any error and you require to remove the account, you can use the PST file to restore Office 365 mailbox items.