Open Outbox In Microsoft Outlook

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Sent emails are remaining in the Outbox instead of sending. My emails are stuck in the outbox and won't send. I cannot send or receive messages, there is just a red 'X' Error: Outlook has detected an issue with an add-on and has disabled it. Error: Not Responding. Microsoft Outlook; Outlook 365; Exchange Online; Microsoft Windows.

Original KB number: 2797572

  1. And down here, on the status bar, it says Outlook is WORKING OFFLINE. When you double-click the email, if you still get an Outlook error, close Outlook, sign out of Windows, sign back in to Windows, and start Outlook. I click and hold the email in the Outbox and drag it to the Drafts folder.
  2. If you leave messages in the Inbox when you exit Outbox, Outlook can send them when you next launch, if you like: Click the File tab, choose Options, and click Advanced.

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.

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 connected option is not enabled, as shown in the following figure from Outlook 2016.

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.

Key: HKEY_CURRENT_USERSoftwareMicrosoftOffice<x.0>OutlookOptionsMail

or

Policy key: HKEY_CURRENT_USERSoftwarePoliciesMicrosoftOffice<x.0>OutlookOptionsMail

DWORD: Send Mail Immediately
Value: 0

Note

In the above registry key paths, <x.0> represents the Outlook version (16.0 = Outlook 2016, Outlook 2019, or Outlook for Office 365, 15.0 = Outlook 2013, 14.0 = Outlook 2010, 12.0 = Outlook 2007, 11.0 = Outlook 2003).

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.
See

Outlook View Outbox

Note

Open Outbox In Microsoft Outlook 365

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.