Fix Message Stuck in Outlook 2019 Outbox Posted on November 10, 2018 by Mitch Bartlett Leave a Comment There are a few reasons a message may get stuck in the Microsoft Outlook 2019 and 2016 Outbox. Hi DJR_810, To clear Outbox, it is recommended that you try the steps below: • Click the Outlook menu> Work Offline; • Create a test email and try to send it. This should make Outbox visible; • Click Outbox to display pending outgoing messages. Edit or delete the messages with large attachments; • If you can’t delete the message, please search the subject to follow the steps above to find and remove it. If the above don’t work, please provide your Outlook for Mac client version details and Mac OS version details for further analysis. Best Regards, Vanessa Hi DJR_810, To clear Outbox, it is recommended that you try the steps below: • Click the Outlook menu> Work Offline; • Create a test email and try to send it. This should make Outbox visible; • Click Outbox to display pending outgoing messages. Edit or delete the messages with large attachments; • If you can’t delete the message, please search the subject to follow the steps above to find and remove it. ![]() ![]() If the above don’t work, please provide your Outlook for Mac client version details and Mac OS version details for further analysis. Best Regards, Vanessa Thanks Vanessa That got me to the Outbox. Then I found the problem was not as expected. Instead it was an email to an incorrectly formatted address (it contained.) that was causing the blockage. Coincidentally someone had sent me a huge email and the 'TOOBIG' error was due to this. Regards Dave. Reason 1 – Recent Password Change Did you recently change your login password? Have a look at the Outbox. If the size for the message is over 5MB in size, it can sit there for a while trying to send. You can let the message sit there and see if it eventually goes, or try to reduce the size of the message. If you have an attachment, try compressing the attachment using. Winzip or using the. Clearing an Item From Outbox If you want to just surrender and delete a message from the Outbox so that you may resend it, here’s the best way to do so. • Exit out of Outlook or go to the “ Send / Receive” tab and select “ Work Offline“. Select “ Start“, then search for “ Outbox” in the Start Search area. • The item(s) in the Outbox should appear in the search. If you want to view and copy the contents of the email before deleting it from the Outbox, you can open it from here. You can also delete it by right-clicking it and selecting “ Delete“.
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