The ones that were just upgraded, did not see the update and emails got stuck in Outlook`s Outbox. So, this issue had nothing to do with SmarterMail, but with Windows 10. If anyone else is experiencing this, I hope this info will help.

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.

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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.

When the message is stuck because it has a large attachment, the Outbox should be visible in the folder list. • Right click on message in Outbox, choose Open Message • Remove the attachment • Press Send This will re-send the message without the over-sized attachment.

If you don't want to send the message, delete it from the outbox instead of removing the attachment. If the Outbox is not visible, and you use Outlook 2016 for Mac, start a Send and Receive then: • Open the Sync Status dialog (1) • Either click the Stop Sync button (2) in the lower left or the little x at the right of the entry to stop the send and receive. • Once you stop the send and receive, the Outbox will be visible (3) in the folder list. If you use Outlook 2011 and don't want to send the message or its stuck for other reason: • Close Outlook 2011 • Hold the Shift key down while reopening Outlook.

• Go to Outbox and delete the stuck message. If the Outbox is not visible, initiate a send and receive and open the Progress dialog. Either click the Stop Sync button in the lower left or the little x at the right of the entry to stop the send and receive. The Outbox should now be visible in message list and you can remove the attachments or delete the message.