When a message gets stuck in your Outbox, the most likely cause is a large attachment.
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Click Send/Receive > Work Offline.
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In the Navigation Pane, click Outbox.
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From here, you can:
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Delete the message. Just select it and press Delete.
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Drag the message to your drafts folder, double-click to open the message, delete the attachment (click it and press Delete).
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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.
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After Outlook closes, start it again and repeat steps 2-3.
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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.
