Most likely there is a communication problem between Outlook and your outgoing mail server, so the email is stuck in Outbox because Outlook can’t connect to your mail server to send it. If you receive an error message while you try to send the email To narrow the cause of the Outbox stuck emails, first of all you should check if you receive an error message while you perform a Send / Receive operation. There can be many reasons why Outlook wouldn’t send an email. This article details possible causes & solutions and it applies to all Outlook versions, including Outlook 2019. Having emails stuck in Outbox is a pretty common issue in Outlook: you’ve wrote an email, clicked to send it, but it stays in the Outbox folder and Outlook is not sending the email, no matter what you do.
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