To release an email stuck in your Drafts or Outbox folder, select one of the sections below.

Email stuck in Outlook 

When a message gets stuck in your Outbox, the most likely cause is a large attachment.

  1. Click Send/Receive > Work Offline.

    The Work Offline button in Outlook 2013

  2. In the Navigation Pane, click Outbox.

  3. From here, you can:

    • Delete the message. Just select it and press Delete.

    • Drag the message to your drafts folder, double-click to open the message, delete the attachment (click it and press Delete).

  4. If an error tells you Outlook is trying to transmit the message, close Outlook. It may take a few moments to exit.

    Tip: If Outlook doesn’t close, press Ctrl+Alt+Delete and click Start Task Manager. In Task Manager, click the Processes tab, scroll down to outlook.exe, and click End Process.

  5. After Outlook closes, start it again and repeat steps 2-3.

  6. After you remove the attachment, click Send/Receive > Work Offline to deselect the button and resume working online.

    Tip: Messages also get stuck in the Outbox when you click Send but you’re not connected. Click Send/Receive and look at the Work Offline button. If it’s blue, you’re disconnected. Click it to connect (the button turns white) and click Send All.

    The Send All button in Outlook 2013

Symptoms

When you send an e-mail message in Microsoft Outlook, the message may remain in your Outbox folder as shown in the following figure.

Outbox in Outlook

When this problem occurs, the message remains in your Outbox folder until you manually initiate a Send/Receive operation (for example, press F9 or select send or receive).

Cause

This problem can occur if the Send immediately when the connected option is not enabled, as shown in the following figure from Outlook 2016.

Send/Receive Outlook option

This setting is tied to the following registry data, so this setting can also be configured by an administrator through a modification of the registry.

Resolution

Use the following steps to re-enable the Send immediately when connected option.

  • Outlook 2010 and later versions

    1. On the File tab, select Options.

    2. In the Outlook Options dialog box, select Advanced.

    3. In the Send and receive section, enable Send immediately when connected.

    4. Select OK.

  • Outlook 2007 and Outlook 2003

    1. On the Tools menu, select Options.

    2. In the Options dialog box, select the Mail Setup tab.

    3. In the Send/Receive section, enable Send immediately when connected.

    4. Select OK.

Note: If you are unable to re-enable this setting because it is grayed out, then the setting is being managed by group policy. In this situation, contact your administrator to have this group policy removed.

ISSUE

After updating to Current Channel Version 1905 (Build 11629.20196) and higher, Outlook may hang at loading profile or won't start. You may notice that if you open Task Manager that other Office processes are unexpectedly listed even though you did not open the application. If you end those processes it may enable Outlook to then open normally.

STATUS: FIXED

On June 25th, 2019, the Outlook Team made a change to the service to fix this issue. If you are still seeing this issue, restart Outlook a couple of times so it can pick up the service change.

WORKAROUND

To work around the issue, you will need to end all Office processes that are running and disable the presence features.

Ending processes in Task Manager

  1. Right click on any space of the Taskbar and select Task Manager.

  2. Under the Processes tab, locate all Office processes.

  3. Select an Office process and then choose End task. Repeat this for each Office process listed.

Disable Outlook presence features

  1. In Outlook, select File, > Options, > People

  2. Uncheck the check boxes for the following options if they are enabled:

    • Display online status next to name

    • Show user photographs when available

  3. Select OK and then restart Outlook.

Note: Disabling the presence functionality will help mitigate the issue. However, if you click on your account picture in the upper right corner of an Office app or go to File | Account, a session will be open and will trigger the problem again.

Symptoms

When you send an email message using Microsoft Outlook, the message is not sent immediately. Instead, it remains in your Outbox folder. This issue does not occur when you start Outlook in Safe mode.

Cause

This problem occurs when both of the following items are true:

  • The Exchange email account is configured to use Cached Exchange mode.

  • You have the following data configured in the Windows registry:

    Outlook 2013, Outlook 2010 or Outlook 2007

    Key: HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\Preferences
    DWORD: LoadTransportProviders
    Value: 1

    Note In this registry subkey, x.0 corresponds to your version of Outlook (15.0 = Outlook 2013, 14.0 = Outlook 2010, 12.0 = Outlook 2007)

Workaround

To work around this issue, use an Online mode profile for your Microsoft Exchange Server mailbox.

Note: This method is a temporary fix. For a permanent fix, see the "Resolution" section.

Resolution

Warning Serious problems might occur if you modify the registry incorrectly by using Registry Editor or by using another method. These problems might require that you reinstall the operating system. Microsoft cannot guarantee that these problems can be solved. Modify the registry at your own risk.

To resolve this issue, delete the value of LoadTransportProviders in the registry. To do this, follow these steps:

  1. Start Registry Editor.

  2. Locate and select the following registry subkey:
     

    HKEY_CURRENT_USER\Software\Microsoft\Office\<x.0>\Outlook\PreferencesNote In this subkey, x.0 corresponds to your version of Outlook (15.0 = Outlook 2013, 14.0 = Outlook 2010, 12.0 = Outlook 2007).

  3. Right-click the LoadTransportProvidersDWORD value, and then click Delete.

  4. Exit Registry Editor.

Email stuck in Outlook.com 

If your emails are not sending from Outlook.com, check these things first:

  1. Check to see if the stuck email is in your Drafts or Outbox folder.

  2. If the message has an attachment that’s larger than 25MB, delete the attachment and either attach a smaller file or upload the file to OneDrive and then attach a link to the attachment. You can then try to send the message again.

  3. If your Inbox is full, you won't be able to send or receive new messages. To make room in your inbox, try emptying your junk folder by right-clicking Junk Email and then selecting the Empty folder.

  4. If you're using Outlook on PC or Mac to send your Outlook.com account email, go to Send/Receive > Send/Receive all folders.

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