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If Outlook is not sending only some Outbox emails, make sure you don’t have the habit to preview / open / click on Outbox emails: your Outbox emails should be unread (marked with bold & italic) otherwise Outlook will not send the email and it will be stuck in your Outbox folder. The problem is likely to be related to your local Outlook configuration. If you do not receive an error message while you try to send the email

You should also check out this list of the most common send & receive error messages and their solutions. – if the above solutions don’t work, use Google and search for the exact error code that you received while you are trying to send the Outlook email: it will likely lead you to a precise solution. The server connection may time out before Outlook gets to send a large email – if you are on a slow Internet connection, make sure your Outbox emails are not supposed to include very large attachments (10 – 20 Mb or more).

– check with your email address provider and make sure you didn’t exceed the hourly / daily email send quota (or other send limits enforced by your email provider)

Occasionally, mail server providers change port numbers or authentication methods, so even if your Outlook account used to send emails without any problems, it may not be working anymore because the outgoing mail server settings were changed – check with your email address provider and make sure your mail server settings are up to date. – check with your Internet service provider to make sure it doesn’t block the port number that you are using for the outgoing mail server (some providers block port 25 or other ports that may be used by an outgoing / SMTP mail server) 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.